[ CAS No. 7328-91-8 ] {[proInfo.proName]}

Name: 7328-91-8|2,2-Dimethylpropane-1,3-diamine|98%
Brand: Ambeed
SKU: A316764
Rating: 91 (29 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 7328-91-8 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 7328-91-8 ]

Product Details of [ 7328-91-8 ]

CAS No. :	7328-91-8	MDL No. :	MFCD00009801
Formula :	C₅H₁₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DDHUNHGZUHZNKB-UHFFFAOYSA-N
M.W :	102.18	Pubchem ID :	81770
Synonyms :

Safety of [ 7328-91-8 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2920
Hazard Statements:	H226-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 7328-91-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 7328-91-8 ]
Downstream synthetic route of [ 7328-91-8 ]

[ 7328-91-8 ] Synthesis Path-Upstream 1~15

1
[ 126-30-7 ]
[ 26734-09-8 ]
[ 7328-91-8 ]

Reference： [1] Angewandte Chemie - International Edition, 1999, vol. 38, # 3, p. 351 - 354

2
[ 762-98-1 ]
[ 7328-91-8 ]

Reference： [1] Industrial and Engineering Chemistry, 1948, vol. 40, p. 507
[2] Journal of the Chemical Society, 1947, p. 1519
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 3814
[4] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1976, vol. 30, p. 21 - 23
[5] Acta Chemica Scandinavica (1947-1973), 1970, vol. 24, p. 1241 - 1246

3
[ 762-98-1 ]
[ 7328-91-8 ]
[ 41882-44-4 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3250
[2] Patent: US2418237, 1944, ,

4
[ 41882-44-4 ]
[ 7328-91-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3789 - 3797

5
[ 922-84-9 ]
[ 7328-91-8 ]

Reference： [1] Patent: US4665210, 1987, A,

6
[ 126-30-7 ]
[ 26734-09-8 ]
[ 7328-91-8 ]

Reference： [1] Angewandte Chemie - International Edition, 1999, vol. 38, # 3, p. 351 - 354

7
[ 5659-93-8 ]
[ 7328-91-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3789 - 3797

8
[ 31044-89-0 ]
[ 7328-91-8 ]

Reference： [1] Journal of Organic Chemistry, 1971, vol. 36, p. 3042 - 3044

9
[ 31044-87-8 ]
[ 7328-91-8 ]

Reference： [1] Journal of Organic Chemistry, 1971, vol. 36, p. 3042 - 3044

10
[ 126-30-7 ]
[ 7328-91-8 ]

Reference： [1] Journal of Organic Chemistry, 1971, vol. 36, p. 3042 - 3044

11
[ 67744-70-1 ]
[ 7328-91-8 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 1502[2] Chem.Abstr., 1948, p. 770

12
[ 114583-17-4 ]
[ 7328-91-8 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 1502[2] Chem.Abstr., 1948, p. 770

13
[ 762-98-1 ]
[ 7328-91-8 ]
[ 41882-44-4 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3250
[2] Patent: US2418237, 1944, ,

14
[ 7328-91-8 ]
[ 24424-99-5 ]
[ 292606-35-0 ]

Yield	Reaction Conditions	Operation in experiment
31.6%	at 0 - 20℃; for 12 h;	To a solution of 2,2-dimethylpropane-1 ,3-diamine (80 g, 783 mmol) in dichloromethane (DCM) (500 mL) at 0 °C was added Boc-anhydride (91 ml_, 391 mmol). It was stirred at ambient temperature for 12 h. The reaction mixture was concentrated. The crude product was purified with column chromatography (Neutral Allumina) by using MeOH : DCM (1 :9) as solvent to give the title compound (50 g, 247 mmol, 31 .6 percent yield) as a white solid. ¹H NMR (400 MHz, CDC ) δ ppm 0.85 (s, 6 H), 1 .44 (s, 9 H), 2.35 - 2.52 (m, 2 H), 3.00 (br d, J=6.14 Hz, 2 H), 5.16 (br s, 1 H). tert-Butyl (2,2-dimethyl-3-(2-nitrophenylsulfonamido)propyl)carbamate

Reference： [1] Patent: WO2018/109648, 2018, A1, . Location in patent: Page/Page column 64
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 2, p. 236 - 246
[3] Patent: US2005/20623, 2005, A1, . Location in patent: Page 116
[4] Patent: EP1550657, 2005, A1, . Location in patent: Page/Page column 46

15
[ 7328-91-8 ]
[ 292606-35-0 ]

Reference： [1] Patent: US2012/178772, 2012, A1,
[2] Chemistry - A European Journal, 2014, vol. 20, # 25, p. 7706 - 7717

[ 7328-91-8 ] Synthesis Path-Downstream 1~60

1
[ 762-98-1 ]
[ 7328-91-8 ]
[ 41882-44-4 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 3250
[2]Patent: US2418237,1944,

2
[ 7328-91-8 ]
[ 2648-71-7 ]
4,8-diaza-3,3,6,6,9,9-hexamethyl-undeca-2,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;

Reference： [1]Nanjappan, Palaniappa; Raju, Natarajan; Ramalingam, Kondareddiar; Nowotnik, David P. [Tetrahedron, 1994, vol. 50, # 29, p. 8617 - 8632]

3
[ 7328-91-8 ]
[ 17768-36-4 ]
3-(5,5-Dimethyl-1,4,5,6-tetrahydro-pyrimidin-2-ylmethyl)-adamantan-1-ol [ No CAS ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 830 - 834

4
[ 7328-91-8 ]
[ 106941-25-7 ]
9-<2-(phosphonomethoxy)ethyl>adenine, cyclic (2',2'-dimethylpropanyl)amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1857 - 1864

5
[ 7328-91-8 ]
[ 130296-37-6 ]
12-(1-hexylheptyl)-3,4-dihydro-3,3-dimethyl-2H-pyrimido<1,2-b>anthra<2,1,9-def:6,5,10-d'e'f'>diisoquinoline-6,11,13(12H)-trione [ No CAS ]
12-(1-hexylheptyl)-3,4-dihydro-3,3-dimethyl-2H-pyrimido<1,2-b>anthra<2,1,9-def:6,5,10-d'e'f'>diisoquinoline-2,6,11,13(12H)-tetrone [ No CAS ]

Reference： [1]Liebigs Annales,1995,p. 481 - 486
[2]Liebigs Annales,1995,p. 481 - 486

6
[ 41882-44-4 ]
[ 7328-91-8 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3789 - 3797

7
[ 7328-91-8 ]
[ 24424-99-5 ]
[ 292606-35-0 ]

Yield	Reaction Conditions	Operation in experiment
31.6%	In dichloromethane; at 0 - 20℃; for 12h;	To a solution of 2,2-dimethylpropane-1 ,3-diamine (80 g, 783 mmol) in dichloromethane (DCM) (500 mL) at 0 C was added Boc-anhydride (91 ml_, 391 mmol). It was stirred at ambient temperature for 12 h. The reaction mixture was concentrated. The crude product was purified with column chromatography (Neutral Allumina) by using MeOH : DCM (1 :9) as solvent to give the title compound (50 g, 247 mmol, 31 .6 % yield) as a white solid. 1H NMR (400 MHz, CDC ) δ ppm 0.85 (s, 6 H), 1 .44 (s, 9 H), 2.35 - 2.52 (m, 2 H), 3.00 (br d, J=6.14 Hz, 2 H), 5.16 (br s, 1 H). tert-Butyl (2,2-dimethyl-3-(2-nitrophenylsulfonamido)propyl)carbamate
	With sodium hydroxide; In water; tert-butyl alcohol; at 0 - 20℃; for 16h;	Water (340 ml) and t-butyl alcohol (200 ml) were added with 2,2-dimethyl-1,3-propylenediamine (25 g), added successively with 4 N aqueous sodium hydroxide (20.5 ml) and a solution of di-t-butyl dicarbonate (21.4 g) in t-butyl alcohol with ice cooling and stirred at room temperature for 16 hours. The solvent (t-butyl alcohol) was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (6 g).
	With triethylamine; In dichloromethane; at 20℃;	2,2-dimetyl-1,3-propanediamine (manufactured by Aldrich Corporation) (2.00 g) was dissolved in anhydrous dichloromethane (100 ml) and then added with triethylamine (2.70 ml) and di-t-butoxydicarbonate (2.14 g), followed by stirring overnight under a nitrogen atmosphere at room temperature. After completion of the reaction, the solution was added with water and stirred, followed by extraction with dichloromethane. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (1.76 g) as a white solid. MS(FAB,Pos.):m/z=203[M+H]+

Reference： [1]Patent: WO2018/109648,2018,A1 .Location in patent: Page/Page column 64
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 236 - 246
[3]Patent: US2005/20623,2005,A1 .Location in patent: Page 116
[4]Patent: EP1550657,2005,A1 .Location in patent: Page/Page column 46

8
[ 7328-91-8 ]
[ 57-71-6 ]
[ 100551-64-2 ]

Reference： [1]Mutation Research - Genetic Toxicology and Environmental Mutagenesis,2000,vol. 465,p. 139 - 144

9
[ 64-17-5 ]
[ 762-98-1 ]
Raney nickel [ No CAS ]
[ 7328-91-8 ]
[ 41882-44-4 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 3250
[2]Patent: US2418237,1944,

10
[ 7647-01-0 ]
[ 114583-17-4 ]
iron powder [ No CAS ]
[ 859065-87-5 ]
[ 7328-91-8 ]
[ 67744-70-1 ]
[ 324763-51-1 ]

Reference： [1]Journal of the Chemical Society,1947,p. 1502
Chem.Abstr.,1948,p. 770
[2]Patent: US2428614,1945,

11
[ 67-56-1 ]
[ 114583-17-4 ]
palladium-CaCO₃ [ No CAS ]
[ 859065-87-5 ]
[ 7328-91-8 ]
[ 67744-70-1 ]
[ 324763-51-1 ]

Reference： [1]Journal of the Chemical Society,1947,p. 1502
Chem.Abstr.,1948,p. 770
[2]Patent: US2428614,1945,

12
[ 67-56-1 ]
[ 114583-17-4 ]
Raney nickel [ No CAS ]
[ 859065-87-5 ]
[ 7328-91-8 ]
[ 67744-70-1 ]
[ 324763-51-1 ]

Reference： [1]Journal of the Chemical Society,1947,p. 1502
Chem.Abstr.,1948,p. 770
[2]Patent: US2428614,1945,

13
[ 114583-17-4 ]
Raney nickel [ No CAS ]
methanolic NH₃ [ No CAS ]
[ 859065-87-5 ]
[ 7328-91-8 ]
[ 67744-70-1 ]
[ 324763-51-1 ]

Reference： [1]Journal of the Chemical Society,1947,p. 1502
Chem.Abstr.,1948,p. 770
[2]Patent: US2428614,1945,

14
[ 75-15-0 ]
[ 7328-91-8 ]
[ 135-73-9 ]
[ 2274-42-2 ]
trifluoroacetic acid [ No CAS ]
[3-Amino-5-(3-amino-2,2-dimethyl-propylamino)-4-methanesulfonyl-thiophen-2-yl]-biphenyl-4-yl-methanone; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 6096 - 6097

15
[ 7328-91-8 ]
[ 57-71-6 ]
2-[1-(hydroxyimino)ethyl]-2,5,5-trimethylperhydropyrimidine-butane-2,3-dione monooxime (1/1) [ No CAS ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,2001,vol. 57,p. 1222 - 1224

16
[ 7328-91-8 ]
[ 62348-13-4 ]
3-methyl-1<i>H</i>-pyrrole-2,4-dicarboxylic acid 4-pentafluorophenyl ester 4-(1,2,2-trimethyl-propyl) ester [ No CAS ]
5-{3-[(isoxazole-5-carbonyl)-amino]-2,2-dimethyl-propylcarbamoyl}-4-methyl-1<i>H</i>-pyrrole-3-carboxylic acid 1,2,2-trimethyl-propyl ester [ No CAS ]

Reference： [1]Il Farmaco,2004,vol. 59,p. 119 - 123

17
[ 7328-91-8 ]
[ 14562-10-8 ]
1,3-diamino-2,2-dimethyl-N,N'-bis(3-phenylsalicylidene)propane [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 4433 - 4451

18
[ 7328-91-8 ]
[ 10111-08-7 ]
C₁₃H₁₈N₆ [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2007,p. 4326 - 4334

19
[ 7328-91-8 ]
[ 31872-62-5 ]
[ 842143-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 100℃; for 5h;	A solution of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (5.00 g, 32.4 MMOL) and 2,2- dimethyl-1, 3-propanediamine (16.2 g, 161 MMOL) in DMF (100 mL) was heated at 100 °C for 5 h. The solvent was removed under reduced pressure to give 7.30 g of the desired COMPOUND. 1H NMR (400 MHz, CDCL3) 8 9.20 (s, 2H), 9.10 (br, 1H), 8.20 (d, 1H), 6.70 (d, 1 H), 3.25 (d, 2H), 2.60 (s, 2H), 1.25 (br, 2H), 0.95 (s, 6H).

Reference： [1]Patent: WO2005/11700,2005,A1 .Location in patent: Page/Page column 78

20
[ 5900-58-3 ]
[ 124-09-4 ]
[ 5162-44-7 ]
[ 446-48-0 ]
[ 7209-38-3 ]
[ 74-96-4 ]
[ 4784-77-4 ]
[ 22288-78-4 ]
[ 542-69-8 ]
bromomethyl resin [ No CAS ]
9-fluorenyl-methoxycarbonyl-cyclohexyl alanine [ No CAS ]
[ 462-94-2 ]
[ 1458-98-6 ]
[ 78-77-3 ]
[ 1809-10-5 ]
[ 110-53-2 ]
[ 592-55-2 ]
[ 7328-91-8 ]
[ 871-76-1 ]
[ 105-83-9 ]
[ 144-48-9 ]
[ 929-59-9 ]
[ 107-59-5 ]
[ 5324-30-1 ]
[ 5428-54-6 ]
[ 27129-86-8 ]
[ 2417-72-3 ]
[ 2581-34-2 ]
[ 554-84-7 ]
[ 3385-21-5 ]
[ 126-38-5 ]
[ 636-93-1 ]
[ 88-30-2 ]
[ 620-13-3 ]
[ 823-78-9 ]
[ 5035-82-5 ]
[ 29022-11-5 ]
[ 539-48-0 ]
[ 35661-39-3 ]
[ 26759-46-6 ]
[ 20439-47-8 ]
[ 2615-25-0 ]
[ 6393-01-7 ]
[ 5372-81-6 ]
[ 35661-40-6 ]
[ 100-39-0 ]
[ 611-17-6 ]
[ 23915-07-3 ]
[ 71989-23-6 ]
[ 35737-15-6 ]
[ 2592-95-2 ]
[ 18880-00-7 ]
[ 88681-68-9 ]
[ 100063-22-7 ]
[ 75-03-6 ]
[ 106-94-5 ]
[ 104-81-4 ]
[ 589-10-6 ]
[ 107-15-3 ]
[ 109-76-2 ]
[ 110-60-1 ]
[ 7051-34-5 ]
[ 106-95-6 ]
[ 622-95-7 ]
[ 589-15-1 ]
[ 134-20-3 ]
[ 2550-36-9 ]
[ 89-92-9 ]
[ 456-41-7 ]
[ 766-80-3 ]
[ 459-46-1 ]
[ 874-98-6 ]
[ 402-49-3 ]
[ 870-63-3 ]
[ 85118-01-0 ]
[ 22115-41-9 ]
[ 3958-57-4 ]
[ 100-11-8 ]
[ 107-82-4 ]
[ 6482-24-2 ]
[ 3132-64-7 ]
[ 112883-41-7 ]
[ 3433-80-5 ]
[ 52727-57-8 ]
C₁₈H₁₅N₂O₃PolS [ No CAS ]
C₂₀H₂₀N₃OPolS [ No CAS ]
C₂₃H₁₉N₂O₂PolS [ No CAS ]
C₁₈H₂₃ClN₃OPolS [ No CAS ]
C₂₂H₂₆N₃OPolS [ No CAS ]
C₂₂H₂₃N₂O₅PolS [ No CAS ]
C₂₀H₂₆ClN₂O₃PolS [ No CAS ]
C₂₃H₂₂ClN₂O₃PolS [ No CAS ]
C₂₀H₂₁FN₃O₃PolS [ No CAS ]
C₂₂H₂₉N₂O₃PolS [ No CAS ]
C₂₁H₂₈N₃O₃PolS [ No CAS ]
C₁₉H₂₆N₃O₄PolS₂ [ No CAS ]
C₂₂H₃₀N₃OPolS [ No CAS ]
C₂₁H₂₈N₃O₄PolS [ No CAS ]
C₂₆H₂₆N₃OPolS [ No CAS ]
C₂₃H₁₅ClF₃N₂O₂PolS [ No CAS ]
C₂₄H₂₂N₃O₃PolS [ No CAS ]
C₂₃H₁₆ClF₂N₂O₂PolS [ No CAS ]
C₂₂H₂₂Br₂N₃OPolS [ No CAS ]
C₂₄H₂₆FN₂O₅PolS [ No CAS ]
C₂₅H₂₂FN₂O₄PolS [ No CAS ]
C₂₆H₂₂N₃O₄PolS [ No CAS ]
C₂₅H₂₅ClN₃O₃PolS [ No CAS ]
C₂₅H₁₈ClF₂N₂O₃PolS [ No CAS ]
C₂₉H₂₆N₃O₃PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; Carbonyldiimidazole; tin-2-ethylhexanoate dihydrate; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; dibromotriphenylphosphorane; In DMF (N,N-dimethyl-formamide); dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane;Combinatorial reaction / High throughput screening (HTS);	EXAMPLE 1 [0213] This example shows the synthesis of a combinatorial library of thioquinazolinone derivatives. [0214] Step 1a: Preparation of Wang Bromide Resin [0215] 40 tea bags containing 2 g each of Wang resin (80 g, 120 mmol) was taken in a 5 L PP container. A solution of triphenylphosphine dibromide (152 g, 0.15 M, 3 eq., 360 mmol) in 2000 ml DCM was added and the solution was shaken at room temperature overnight. The resin was sequentially washed with DCM (4×, 1.5 L each) and diethylether (6×, 1.5 L each) and dried under vacuum, to give the bromo wang resin. [0216] Step 1b: Loading of the Nitrophenol on Bromo Wang [0217] 20 g of the Bromo wang resin (1.5 meq/g) was taken in a 2 L wide-mouthed glass container and 1000 mL DMA was addded to it followed by the addition of the nitro phenol (10 eq., 0.3M, 300 mmol). Potasium t-butoxide (33.46 g, 10 eq., 300 mmol) was then added to it and the bottles were heated at 50 C. overnight. The bags were washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The tea bags were then dried overnight in air. The following nitrophenols were used: [0218] 2-METHYL-5-NITROPHENOL [0219] 5-HYDROXY-2-NITROBENZOTRIFLUORIDE [0220] 3-METHYL-4-NITROPHENOL [0221] 2-METHOXY-5-NITROPHENOL [0222] M-NITROPHENOL [0223] Step 1c: Reduction of the Nitro Group to Amine [0224] A 2.0 M solution of tin-2-ethylhexanoate dihydrate was prepared in DMF containing 0.5% H2O. The tea bags were added and the solution is heated at 50 C. for 40 hours. After cooling the bags are washed with DMF/10% HOAc (3×), DMF (3×), 5% DIEA/DCM (2×), DCM (2×) and MeOH (2×) and dried in air overnight. [0225] Step 1d: Coupling N-FMOC Protected Amino Acid to Wang Resin. [0226] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL plastic bottle. DMF (300 mL), DCM (300 mL), FMOC-Cyclohexyl alanine (70.82 g, 6 eq., 0.3M, 180 mmol), DIC (22.71 g, 6 eq., 180 mmol), HOBt (24.32 g, 6 eq., 180 mmol) were added sequentially. After shaking for 12 hours, the packet was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried overnight in air. The tea bags containing the amino acids were then treated with 20% piperidine/DMF for 2 h at room temperature to deblock the FMOC group. The following amino acids were used: [0227] FMOC-GLY-OH [0228] FMOC-ALA-OH [0229] FMOC-L-ISOLEUCINE [0230] FMOC-L-PHENYLALANINE [0231] FMOC-D-NLE-OH [0232] FMOC-CHA-OH [0233] FMOC-L-TRYPTOPHAN [0234] Step 1e: Coupling of the Diamines to Wang Resin [0235] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL Nalgene bottle. 600 mL of DCM was added followed by the addition of the carbonyl diimidazole (29.9 g, 6 eq., 0.3M, 180 mmol) and the flasks were shaken at room temperature for 3 hours after which they were decanted and washed with DCM (2×, 600 mL). To these Nalgene bottles were added the diamines (6 eq., 0.4M, 180 mmol) in 450 mL of DCM (0.4M) and they were shaken at room temperature overnight. The diamines used were as follows: [0236] 2,2-DIMETHYL-1,3-PROPANEDIAMINE [0237] 1,3-CYCLOHEXANEDIAMINE [0238] (1R,2R)-(-)-1,2-DIAMINOCYCLOHEXANE [0239] TRANS-1,4-DIAMINOCYCLOHEXANE [0240] P-XYLYLENEDIAMINE [0241] 1,4-BIS(3-AMINOPROPYL)PIPERAZINE [0242] ETHYLENEDIAMINE [0243] 1,3-DIAMINOPROPANE [0244] 1,8-DIAMINO-3,6-DIOXAOCTANE [0245] 1,4-DIAMINOBUTANE [0246] 1,5-DIAMINOPENTANE [0247] 1,6-HEXANEDIAMINE [0248] N,N-BIS(3-AMINOPROPYL)METHYLAMINE [0249] 2,2'-THIOBIS(ETHYLAMINE) [0250] 2,5-DIMETHYL-1,4-PHENYLENEDIAMINE [0251] After shaking overnight, the packets was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried in air. [0252] Step 2: Formation of the Isothiocyanate [0253] The o-amino benzoate ester (136 g, 10 eq., 900 mmol) was taken in a 5 L wide-mouthed glass bottle and 2.7 L of dichloroethane was added to it (0.3M). The following esters were used: [0254] METHYL ANTHRANILATE [0255] METHYL 2-AMINO-4-CHLOROBENZOATE [0256] 2-AMINO-4,5-DIMETHOXYBENZOIC ACID [0257] METHYL ESTER [0258] METHYL 3,4,5-TRIMETHOXYANTHRANILATE [0259] DIMETHYL AMINOTEREPHTHALATE [0260] METHYL 2-AMINO-5-BROMOBENZOATE [0261] METHYL 3-AMINOTHIOPHENE-2-CARBOXYLATE [0262] METHYL 3-AMINO-5-PHENYLTHIOPHENE-2-CARBOXYLATE [0263] Thiocarbonyl diimidazole (160 g, 10 eq., 900 mmol) was added to it and the solution was heated at 55 C. overnight to form the isothiocyanate. [0264] Step 3: Formation of the Thioquinazolinone [0265] The next day the tea bags containing the amino acids, diamines and the amino phenols on wang resin (90 mmol) was added to the isothiocyanate solution from reaction 2 and the glass bottles were heated at 55 C. overnight. After cooling the bags was washed alternatively with DMF (2000 mL) and DCM (2000 mL) 3 cycles followed by 6 cycles of MeOH...

Reference： [1]Patent: US2004/102629,2004,A1 .Location in patent: Page 16-18

21
[ 7328-91-8 ]
[Ni(1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid(-2H))(H₂O)4]*H₂O [ No CAS ]
[ 65-86-1 ]
[ 1207096-31-8 ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2009,vol. 635,p. 577 - 581

22
[ 7328-91-8 ]
[ 84501-28-0 ]
C₃₄H₄₈N₄O₂*2ClHO₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 931 - 933

23
[ 7328-91-8 ]
[ 938-18-1 ]
[ 1203602-81-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In dichloromethane at 0 - 25℃; for 12h;	2.1 N,N'-(2,2-dimethylpropane-1,3-diyl)bis(2,4,6-trimethylbenzamide)Synthesis: Weigh a certain molar amount of 2,2-dimethylpropanediamine in a round bottom flask, and then weigh the amount of the acid-binding agent triethylamine in a molar ratio of 1:1.2, and also pour into the round bottom flask. Add appropriate amount of dichloromethane solvent, and weigh 2,4,6-trimethylbenzoyl chloride in a molar ratio of 2:1. After diluting 2,4,6-trimethylbenzoyl chloride with dichloromethane, Slowly drip into the ice bath reaction in a round bottom flask.After the dropwise addition of 2,4,6-trimethylbenzoyl chloride, the ice bath was removed, and the reaction was stopped after 12 hours at room temperature. The reaction solution was washed once with 25 mL of 1 mol of L-1 sodium hydroxide.Then, it was washed twice with 25 mL of 1 mol of L-1 hydrochloric acid, once with 25 mL of 1 mol of L-1 sodium hydroxide, and finally with twice with saturated brine. After collecting the organic layer and removing the solvent,Obtained a white solid, dried under an infrared lamp, and recrystallized from anhydrous methanol.Get the product,The yield was 85%.
67%	With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN104817583, 2019, B Location in patent: Paragraph 0025; 0060-0062
[2]Leitch, David C.; Payne, Philippa R.; Dunbar, Christine R.; Schafer, Laurel L. [Journal of the American Chemical Society, 2009, vol. 131, # 51, p. 18246 - 18247]

24
[ 627-42-9 ]
[ 7328-91-8 ]
[ 1295636-93-9 ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1359 - 1366

25
[ 7328-91-8 ]
[ 72968-07-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: water 2: NaNO₃; AgNO₃; KOH / acetone; water

Reference： [1]Van Kralingen, Cornelis G.; Reedijk, Jan; Spek, Anthony L. [Inorganic Chemistry, 1980, vol. 19, # 6, p. 1481 - 1485]

26
[ 7328-91-8 ]
[ 13623-94-4 ]
[ 1353880-58-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol at 80℃; for 2.5h;
92%	In ethanol Reflux;
87%	In ethanol for 8h; Reflux;

	for 12h; Reflux;	4.3. General procedure for the preparation of compounds 2-4, exemplified on 2CommentComment General procedure: A mixture of cyclohexane-1,2-diamine (0.11 g, mmol), 1,1-bis(methylthio)-2-nitroethylene (0.16 g, 1 mmol) in a 50 mL flask was stirred at reflux for 12 h, then N,N'-bis(phenylmethylidene)phenylmethanediamine 1a (0.3 g, 1 mmol) was added and the reaction mixture heated at reflux for the time period as indicated in refPreviewPlaceHolderTable 1. When the reaction mixture was cooled to room temperature, a white solid precipitated. The precipitates were filtered and washed with diethyl ether to give product 2 in 74% yields. All products gave satisfactory spectral data in accordance with the assigned structures.
	In ethanol for 0.5h; Reflux;	4.2 General procedure for the preparation of 2-oxopyridine-fused 1,3-diazaheterocycles 4 General procedure: Diamine 1 (1.0 mmol) and ketene dithioacetal 2 (1.5 equiv) was mixed and dissolved in EtOH (5 mL). After stirring for 0.5 h under reflux, methyl 2-perfluoroalkynoate 3 (1.1 equiv) was added dropwise into the solution. The reaction mixture was then allowed to stir under reflux for the rest of the designated time (see Table 2). Evaporation of the solvent under reduced pressure resulted in crude product, which was subjected to column chromatography on silica gel for further purification using ethyl acetate/petroleum ether as eluent.
	In acetonitrile Reflux;
	In ethanol for 3h; Reflux;
	In ethanol at 78℃; for 2h;	General procedure for preparation of 3a General procedure: A mixture of 1,1-bis(methylsulfanyl)-2-nitroethene (1 mmol) and diamine 1a (1 mmol) in EtOH (3 mL) was heated at reflux temperature for 2 h. Then 3-formylchromone 2a (1 mmol) was added to the reaction mixture at room temperature. Upon completion (3 h), monitored by thin layer chromatography (TLC), the mixture was filtered and the precipitate was washed with distilled water (2 mL) and EtOH (5 mL) to afford the pure product 3a.
	In ethanol; water for 6h; Reflux;
	for 3h; Reflux;	General Procedure for the Synthesis of Compound 4a-g General procedure: 2-Chloroquinoline-3-carbaldehyde (1 mmol), malononitrileor ethyl 2-cyanoacetate (1 mmol) and piperidine(1 drop: 0.0093 g, 0.109 mmol, 11 mol%) were stirred in ethanol at room temperature for 1 h to obtain Knoevenagel condensation compounds containing quinoline scaffold.Simultaneously, in another pot, nitroketen aminals were prepared through the reaction of aliphatic diamines (1 mmol)and 1,1-bis(methylthio)-2-nitroethylene (1 mmol) at reflux conditions for 3 h. After completion of the reactions (monitored by TLC), the solutions were mixed and stirred for2-3 h to achieve pyrido[1,2-a]pyrimidines or imidazo[1,2-a]pyridines 4 depending on the diamine used for the reaction.

Reference： [1]Safari, Ensieh; Maryamabadi, Ammar; Hasaninejad, Alireza [RSC Advances, 2017, vol. 7, # 63, p. 39502 - 39511]
[2]Location in patent: experimental part Kalisiak, Jarosław; Ralph, Erik C.; Cashman, John R. [Journal of Medicinal Chemistry, 2012, vol. 55, # 1, p. 465 - 474]
[3]Fan, Yefeng; Liu, Song; Chen, Nanyang; Shao, Xusheng; Xu, Xiaoyong; Li, Zhong [Synlett, 2015, vol. 26, # 3, p. 393 - 403]
[4]Location in patent: experimental part Alizadeh, Abdolali; Mokhtari, Javad; Ahmadi, Mehdi [Tetrahedron, 2012, vol. 68, # 1, p. 319 - 322]
[5]Wang, Zewei; Sun, Tianqi; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo [Tetrahedron, 2013, vol. 69, # 21, p. 4270 - 4275]
[6]Alizadeh, Abdolali; Moafi, Leila [Helvetica Chimica Acta, 2015, vol. 98, # 4, p. 546 - 551]
[7]Alizadeh, Abdolali; Ghanbaripour, Rashid; Weng Ng, Seik [Helvetica Chimica Acta, 2015, vol. 98, # 5, p. 663 - 667]
[8]Alizadeh, Abdolali; Bayat, Fahimeh; Zhu, Zhe [Research on Chemical Intermediates, 2016, vol. 42, # 6, p. 5927 - 5936]
[9]Hosseini, Hajar; Bayat, Mohammad [RSC Advances, 2019, vol. 9, # 13, p. 7218 - 7227]
[10]Alizadeh, Abdolali; Roosta, Atefeh; Rezaiyehraad, Reza [Journal of the Iranian Chemical Society, 2020, vol. 17, # 5, p. 1123 - 1130]

27
[ 7328-91-8 ]
[ 29754-58-3 ]
C₂₅H₂₆N₂O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1213 - 1218

28
[ 7328-91-8 ]
[ 29754-58-3 ]
[ 1355183-61-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1213 - 1218

29
[ 7328-91-8 ]
[ 52784-31-3 ]
C₂₁H₂₆N₂ [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 772 - 775

30
[ 7328-91-8 ]
[ 292606-35-0 ]

Reference： [1]Patent: US2012/178772,2012,A1
[2]Chemistry - A European Journal,2014,vol. 20,p. 7706 - 7717

31
[ 938-24-9 ]
[ 7328-91-8 ]
[ 13623-94-4 ]
[ 109-77-3 ]
5c-amino-2,2-dimethyl-5-nitro-6-oxo-1,2,3,4-tetrahydro-6H-5d-oxa-4,10c-diazabenzo[2,3]1-azapentaleno[3a,6a-a]inden-5-yl cyanide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In ethanol for 11h;	General synthesis procedure: (for example, 3a) General synthesis procedure: (for example, 3a) To a solution of ninhydrin (1 mmol) and malononitrile in EtOH (4 mL) was added triethylamine (0.1 mmol), and the solution was stirred for 1 h at room temperature. Then, nitro ketene dithioacetal 1 (1 mmol) and propyldiamine 2 (1 mmol) were added in sequence. Upon completion (11 h), monitored by TLC, the mixture was filtered and the precipitate washed with EtOH (4 mL) to afford the pure product 3a.

Reference： [1]Rezvanian, Atieh; Alizadeh, Abdolali [Tetrahedron, 2012, vol. 68, # 49, p. 10164 - 10168,5]

32
[ 7328-91-8 ]
[ 84501-28-0 ]
C₃₄H₅₀N₄O₂^(6-)*2ClO₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		4-tert-Butyl-2,6-diformylphenol (2.68 g, 13.0 mmol), sodium perchlorate (6.27 g, 51.2 mmol) and acetic acid (1.47 mL, 25.7 mmol) were dissolved in methanol (180 mL). The solution was stirred and heated to 70 C. When the mixture started to reflux, 2,2-dimethyl-1,3-propanediamine (1.56 mL, 13.0 mmol) in methanol (60 mL) was added dropwise. Thereafter, the heating was switched off and the mixture stirred overnight at room temperature. All volatiles were removed in vacuo affording to a bright orange solid. The solid was filtered off, washed three times with cold ethanol and diethyl ether (-78 C) and dried to give a bright orange product (9.22 g, 11.7 mmol, 90 % yield).C34H50Cl2N4O10 (745.69 g/mol); 1H NMR (400 MHz, DMSO d6) delta/ppm = 13.60 (4H, br s, NH/OH), 8.66 (4H, d, N=CH), 7.64 (4H, s, Ar-H), 3.86 (8H, s, CH2), 1.27 (12H, s, CH3), 1.13 (18H, s, CH3); 13C APT NMR (125 MHz, DMSO d6) delta/ppm = 176.5, 169.3, 142.5, 136.2, 116.6, 56.0, 45.8, 34.8. Comparison of the NMR spectra with reported values confirms the chemical structure of the product as [H4L](ClO4)2 [1,2].

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 42 - 49

33
[ 7328-91-8 ]
[ 16634-88-1 ]
C₁₉H₁₈Br₂N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In methanol; for 3.0h;Reflux;	Schematic representation of the synthesis procedures is shown in scheme 1. For this ligand, to a vigorously stirred and boiling solution of <strong>[16634-88-1]5-bromo-2-hydroxy-3-nitrobenzaldehyde</strong> (0.25 g, 1 mmol) in 15 mL methanol was added a solution of 0.52 g (0.5 mmol) 2,2-dimethyl-1,3-propanediamine in 15 mL methanol. The reaction mixture was refluxed for 3 h while the progress of the reaction was monitored by TLC. The solid orange product was collected by filtration, washed with 10 mL of boiling methanol and air dried to yield 0.43 g of the target ligand (78%). m.p. = 216-217 C. Selected IR (cm-1): 3467, 1647, 1508. 1H NMR (DMSO-d6): 14.82 (2H, br), 8.66 (2H, s), 8.12 (2H, d), 7.82 (2H, d), 3.64 (4H, s), 1.03 (6H, s). UV-Vis. 10-5 M solution in DMF [lambdamax nm, (epsilon M-1 cm-1)]: 267 (14,300), 471 (15,500). Anal. Calcd for C19H18Br2N4O6: C, 40.88; H, 3.25; N, 10.04. Found: C, 40.79; H, 3.20; N, 10.10.

Reference： [1]Journal of Coordination Chemistry,2015,vol. 68,p. 2296 - 2306
[2]Journal of Coordination Chemistry,2016,vol. 69,p. 190 - 198

34
[ 7328-91-8 ]
[ 16634-88-1 ]
C₁₉H₁₆Br₂CuN₄O₆ [ No CAS ]

Reference： [1]Journal of Coordination Chemistry,2015,vol. 68,p. 2296 - 2306

35
[ 7328-91-8 ]
[ 50910-55-9 ]
(N¹E,N³E)-N¹,N³-bis(2-amino-3,5-dibromobenzaldehyde)-2,2-dimethyl-propan-1,3-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In methanol; at 70℃; for 12h;	General procedure: solution (20 mL) of <strong>[50910-55-9]2-amino-3,5-dibromobenzaldehyde</strong>(0.278 g, 2 mmol), aliphatic diamine (1 mmol) was added.The bright yellow solution was stirred and heated to reflux for12 h. A white precipitate was obtained that was filtered off, andthen washed with mixture of ethylacetate and n-hexan (1:1). Thegeneral synthesis Scheme of Schiff bases L1-L4 has been shownin Scheme 1.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 146,p. 221 - 227

36
[ 117-99-7 ]
[ 7328-91-8 ]
[ 222558-57-8 ]

Yield	Reaction Conditions	Operation in experiment
74.5%	In methanol for 5h; Reflux;	2.2.1. Preparation of 2,2′-((2,2-dimethylpropane-1,3-diyl)bis((nitrilo)(phenylmethylidyne)))-diphenol (SchB) The Schiff base (scheme 1) was synthesized according to the method described in previous papers [12]. A solution of 10 mmol 2-hydroxybenzophenone and 5 mmol 2,2-dimethyl-1,3-propanediamine in 60 mL of methanol was refluxed for 5 h. The excess of the solvent (ca. 50 mL) was then evaporated. After cooling to 4 °C, a yellow solid was produced. The polycrystalline product was collected by filtration, washed with methanol, and dried (74.5% yields). Elemental analysis of C31H30N2O2, Calcd (%): C,80.49; H, 6.54; N, 6.06. Found: C, 80.41; H, 6.63; N, 5.98.
74.5%	In methanol at 65℃; for 2h;	Preparation of Schiff bases General procedure: The Schiff base ligands were synthesized (Scheme 1) using a similar method described in previous papers [1, 25-27]. Mixtures of 10 mmol of appropriate ketone and 5 mmol of diamine in 40 mL of methanol were refluxed for 2 h. The excess of the solvent (ca. 30 mL) was then evaporated. After cooling to 4 C, yellow solids were formed. The products were collected by filtration, washed with cold methanol and dried in air.

Reference： [1]Bartyzel, Agata; Kaczor, Agnieszka A. [Journal of Coordination Chemistry, 2015, vol. 68, # 20, p. 3701 - 3717]
[2]Bartyzel, Agata [Journal of Thermal Analysis and Calorimetry, 2018, vol. 131, # 2, p. 1221 - 1236]

37
[ 7328-91-8 ]
[ 153759-58-1 ]
C₂₇H₃₆Br₂N₂O₂ [ No CAS ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 1215 - 1224

38
[ 7328-91-8 ]
[ 464-49-3 ]
(N¹E,N³E)-2,2-dimethyl-N¹,N³-bis(1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)pentane-1,3-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.4%	With toluene-4-sulfonic acid In toluene at 150℃; for 96h; Dean-Stark;	2.2.2 Synthesis of BCP 2,2-Dimethylpropane-1,3-diamine (2.54 g, 24.00 mmol), 2 equiv. (1R)-(+)-camphor (7.56 g, 49.00 mmol), and p-TsOH (1.00 g, 5.20 mmol) were dissolved in toluene (50 mL), and the solution was heated under reflux in a Dean-Stark trap. The reaction mixture was stirred at 150 °C for four days and washed with H2O (3 × 20 mL). The organic phase was dried over MgSO4. The solvent was evaporated to give yellow oil (7.96 g, 86.4%). 1H NMR (CDCl3, 400 MHz, 298 K): δ = 3.92-3.67 (m, 4H, propylene-CH2), 2.79-2.68 (m, 2H, camphor-H), 2.56 (s, 3H, propylene-CH3), 2.48 (s, 3H, propylene-CH3), 2.06-2.02 (m, 2H, camphor-H), 2.02-2.98 (m, 2H, camphor-H), 1.95-1.78 (m, 4H, camphor-H), 1.56-1.51 (m, 2H, camphor-H), 1.46 (s, 6H, camphor-CH3), 1.26-1.20 (m, 2H, camphor-H), 0.94 (s, 6H, camphor-CH3), 0.78 (s, 6H, camphor-CH3). 13C NMR (CDCl3, 100 MHz, 298 K) δ = 195.1 (1C, C = N), 59.9 (1C, N-CH2-C-CH2-N), 57.7 (1C, N-CH2-C-CH2-N), 55.1 (2C, camphor-C), 49.4 (2C, camphor-C), 45.9 (2C, camphor-C), 40.3 (2C, camphor-C), 35.6 (1C, N-CH2-C-CH2-N), 33.2 (2C, camphor-C), 31.2 (2C, camphor-C), 30.1 (2C, camphor-C), 27.4 (2C, CH3-C-CH3), 24.3 (2C, camphor-CH3), 22.2 (2C, camphor-CH3), 19.4 (2C, camphor-CH3). IR (solid neat; cm-1): 2965 (w), 1615 (w), 1492 (m), 1451 (w), 1377 (m), 1282 (w), 1194 (m), 1087 (s), 1063 (s), 1014 (s), 972 (s), 934 (w), 871 (w), 760 (s), 693 (s), 621 (m), 563 (w).

Reference： [1]Kwon, Kyuong Seop; Nayab, Saira; Lee, Hong-In; Jeong, Jong Hwa [Polyhedron, 2017, vol. 126, p. 127 - 133]

39
[ 83-72-7 ]
[ 7328-91-8 ]
[ 1074-12-0 ]
[ 13623-94-4 ]
2-(3,3-dimethyl-8-nitro-6-phenyl-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidin-7-yl)-3-hydroxy-[1,4]naphthoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 2,2-Dimethyl-1,3-diaminopropane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux; Stage #2: 2-hydroxynaphtho-1,4-quinone; phenylglyoxal hydrate In ethanol; water at 60℃; for 0.25h; regioselective reaction;	General procedure: A mixture of 1,4-diaminobutane(100 mL, 1 mmol), 1,1-bis(methylthio)-2-nitro ethylene (0.165 g, 1 mmol) and12 mL H2O/EtOH (3:1, v-v) in a 50 mL flask was heated at reflux for 4 h. Afterreaction completion (monitored by TLC, ethyl acetate/n-hexane, 6:4), arylglyoxal (0.152 g, 1 mmol), 2-hydroxy-1,4-naphthoquinone (0.174 g, 1 mmol)were added to the reaction mixture, and it was stirred Under 60 C for a periodof time shown in Table 2. Then, the reaction mixture was cooled to roomtemperature and filtered to give the crude product. The solid was washed witha mixture of water and ethanol to give product 5a in 95% yield

Reference： [1]Bayat, Mohammad; Nasri, Shima [Tetrahedron Letters, 2017, vol. 58, # 32, p. 3107 - 3111]

40
[ 83-72-7 ]
[ 7328-91-8 ]
[ 403-32-7 ]
[ 13623-94-4 ]
2-[6-(4-fluoro-phenyl)-3,3-dimethyl-8-nitro-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidin-7-yl]-3-hydroxy-[1,4]naphthoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 2,2-Dimethyl-1,3-diaminopropane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux; Stage #2: 2-hydroxynaphtho-1,4-quinone; (4-fluorophenyl)glyoxal In ethanol; water at 60℃; for 0.0833333h; regioselective reaction;	General procedure: A mixture of 1,4-diaminobutane(100 mL, 1 mmol), 1,1-bis(methylthio)-2-nitro ethylene (0.165 g, 1 mmol) and12 mL H2O/EtOH (3:1, v-v) in a 50 mL flask was heated at reflux for 4 h. Afterreaction completion (monitored by TLC, ethyl acetate/n-hexane, 6:4), arylglyoxal (0.152 g, 1 mmol), 2-hydroxy-1,4-naphthoquinone (0.174 g, 1 mmol)were added to the reaction mixture, and it was stirred Under 60 C for a periodof time shown in Table 2. Then, the reaction mixture was cooled to roomtemperature and filtered to give the crude product. The solid was washed witha mixture of water and ethanol to give product 5a in 95% yield

Reference： [1]Bayat, Mohammad; Nasri, Shima [Tetrahedron Letters, 2017, vol. 58, # 32, p. 3107 - 3111]

41
[ 83-72-7 ]
[ 7328-91-8 ]
[ 13623-94-4 ]
[ 78-98-8 ]
2-hydroxy-3-(3,3,6-trimethyl-8-nitro-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidin-7-yl)-[1,4]naphthoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 2,2-Dimethyl-1,3-diaminopropane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux; Stage #2: 2-hydroxynaphtho-1,4-quinone; 2-oxopropanal In ethanol; water at 60℃; for 0.5h; regioselective reaction;	General procedure: A mixture of 1,4-diaminobutane(100 mL, 1 mmol), 1,1-bis(methylthio)-2-nitro ethylene (0.165 g, 1 mmol) and12 mL H2O/EtOH (3:1, v-v) in a 50 mL flask was heated at reflux for 4 h. Afterreaction completion (monitored by TLC, ethyl acetate/n-hexane, 6:4), arylglyoxal (0.152 g, 1 mmol), 2-hydroxy-1,4-naphthoquinone (0.174 g, 1 mmol)were added to the reaction mixture, and it was stirred Under 60 C for a periodof time shown in Table 2. Then, the reaction mixture was cooled to roomtemperature and filtered to give the crude product. The solid was washed witha mixture of water and ethanol to give product 5a in 95% yield

Reference： [1]Bayat, Mohammad; Nasri, Shima [Tetrahedron Letters, 2017, vol. 58, # 32, p. 3107 - 3111]

42
[ 7328-91-8 ]
[ 492-88-6 ]
N,N′-bis(3-ethoxysalicylidene)2,2-dimethyl-1,3-propanediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.4%	In methanol at 80℃; for 3h; Reflux;	2.5. Synthesis of N,N'-bis(5-bromo-3-methoxysalicylidenimino)-1,3-diaminopropane and N,N'-bis(3-ethoxysalicylidene)-2,2-dimethyl-1,3-propanediamine General procedure: Pro-ligands (H2L1-H2L2) have been synthesized in our laboratoryfollowing the literature method (Scheme 1) [45]. The refluxcondensation of 5-bromo-3-methoxy-2-hydroxybenzaldehyde(0.231 g, 1 mmol) with 1,3-diaminopropane (0.0371 g, 0.5 mmol)in (50 mL) methanol at 80 °C for 3 h prepared H2L1. A similar procedurewas used for the synthesis of H2L2 except 2,2-dimethyl-1,3-propanediamine (0.0511 g, 0.5 mmol) condensed with 3-ethoxy-2-hydroxybenzaldehyde (0.166 g, 1 mmol). The solvent was removedunder vacuum and the yellow powder product separated out upon cooling the solution which was collected and air-dried. N,N'-bis(5-bromo-3-methoxysalicylidenimino)-1,3-diaminopropane (H2L1):Yield: 0.215 g (85.8%)
89.4%	In methanol at 80℃; for 3h;	2.5. Synthesis of N,N′ -bis(5-2.5. Synthesis of N,N′ -bis(5-bromo-3-methoxysalicylidenimino)-1,3-diaminopropane (H2L1) and N,N′ -bis(3-ethoxysalicylidene)-2,2-dimethyl-1,3-propanediamine (H2L2) General procedure: Two Salen ligands have been synthesized following the literaturemethod (Scheme1) [42a]. The refllux condensation of 5-Bromo-3-methoxy-2-hydroxybenzaldehyde (0.231 g, 1 mmol) with 1,3-diaminopropane(0.0371 g, 0.5 mmol) in (50 mL) methanol at 80 °C for 3hr prepared H2L1. An identical procedure was used to synthesize H2L2 except 2,2-dimethyl-1,3-propanediamine (0.0511 g, 0.5 mmol)condensed with 3-ethoxy-2-hydroxybenzaldehyde (0.166 g, 1 mmol). Finally, the solvent was removed under vacuum and the yellow powderproduct separated upon cooling, the solution collected and air-dried.
87%	In methanol for 1h; Reflux;	General procedure: To a stirred MeOH (20 mL) solution of 3-ethoxy-salicylaldehyde (0.66 g, 4 mmol) was added a MeOH (20 mL) solution of 4,5-dimethyl-1,2-phenylenediamine (0.27 g,2 mmol) or 2,2-dimethyl-1,3-propanediamine (0.21 g,2 mmol). The reaction mixture was heated at reflux for 1 h,and upon cooling to room temperature, the resulting precipitate was collected by suction filtration and washed with cold MeOH (3 9 10 mL) to afford the desired Schiff base.

	In methanol for 2h;
	In acetonitrile for 1h;
	In methanol Reflux;
	In methanol for 1h; Reflux;
	In methanol for 1h; Reflux;	2.1.1 2.1.1 Preparation of H₂L¹ [N,N′-bis(3-ethoxysalicylidene)-2,2-dimethylpropane-1,3-diamine] and H₂L² [N,N′-bis(3-methoxysalicylidene)-2,2-dimethylpropane-1,3-diamine] A 10 methanol solution (10mL) of 11 3-ethoxysalicylaldehyde (332mg, 2mmol) and 12 2,2-dimethyl-1,3-diaminopropane (0.13mL, 1mmol) was refluxed for ca. 1h to form H2L1.
	In methanol for 0.1h; Reflux;
	In methanol for 1h; Reflux;	2.2.2 Preparation of [Fe(L²)(HL³)]ClO₄ (2) {H₂L² = N,N′-bis(3-ethoxysalicylidene)2,2-dimethyl-1,3-propanediamine and HL³ = 2-((3-amino-2,2-dimethylpropylimino)methyl)-6-ethoxyphenol} A methanol solution of (20mL) 2,2-dimethyl-1,3-diaminopropane (0.12mL, 1mmol) and 3-ethoxysalicyldehyde (332mg, 2mmol) was refluxed for ca. 1h to form a Schiff base ligand, H2L2. Iron(III) perchlorate hydrate (354mg, 1mmol) was added to the methanol solution of the Schiff base ligand, H2L2 under stirring condition to produce a deep red coloured solution. A methanol solution (10mL) of 3-ethoxysalicyldehyde (166mg, 1mmol) was then slowly added to it, followed by the addition of a methanol solution (10mL) of 2,2-dimethyl-1,3-diaminopropane (0.12mL, 1mmol) and the stirring was continued for additional 2h. Diffraction quality green coloured single crystals of complex 2 were obtained after few days on slow evaporation of the solution in open atmosphere. (0008) Yield: 514mg (∼64%); based on iron(III). Anal. Calc. for C37H50FeN4O10Cl (FW=802.11): C, 55.35; H, 6.23; N, 6.98. Found: C, 55.3; H, 6.2; N, 7.0%. FT-IR (KBr, cm-1): 3212, 3175 (νN-H), 2970-2868 (νC-H), 1620 (νC=N), 2082 (νClO4). UV-VIS [λmax (nm)] [εmax (Lmol-1cm-1)] (acetonitrile): 232 (2.52×104); 269 (1.49×104); 334 (4.58×103); 528 (1.90×103).
	In methanol for 2h; Reflux;
	In methanol for 1h; Reflux;
	In ethanol for 1h; Reflux;
	In methanol for 2h; Reflux;	2.2.1.1. Synthesis of H2La [N,N'-bis(3-methoxysalicylidene)-2,2-dimethyl-1,3-propanediamine], H2Lb [N,N'-bis(3-ethoxysalicylidene)-2,2-dimethyl-1,3-propanediamine], H2Lc [N,N'-bis(3-methoxysalicylidene)-1,3-propanediamine] and H2Ld [N,N'-bis(3-ethoxysalicylidene)-1,3-propanediamine] General procedure: A methanol solution(10 mL) of 2,2-dimethyl-1,3-propanediamine (1 mmol, 0.12 mL)was mixed separately with of 3-methoxysalicylaldehyde (2 mmol,304 mg) and 3-ethoxysalicylaldehyde, (2 mmol, 332 mg) and theresulting solutions were allowed to reflux for ca. 2 h to synthesizetwo hexadentate N2O4 donor Schiff base ligands, H2La [N,N'-bis(3-ethoxysalicylidene)2,2-dimethyl-1,3-propanediamine] andH2Lb [N,N'-bis(3-ethoxysalicylidene)-2,2-dimethyl-1,3-propanediamine]respectively. Other two hexadentate Schiff bases, H2Lc [N,N'-bis(3-methoxysalicylidene)-1,3-propanediamine] and H2Ld [N,N'-bis(3-ethoxysalicylidene)-1,3-propanediamine] were synthesized followingthe similar procedure as mentioned above except 1,3-propanediamine(1 mmol, 0.11 mL) was used as the diamine instead of2,2-dimethyl-1,3-propanediamine.
	In methanol for 0.2h; Reflux;	A Schiff base ligand, H2L’ {H2L’ = N,N’-bis(3-ethoxysalicylidene)-2,2-dimethyl-propane-1,3-diamine} was prepared by refluxing2,2-dimethylpropane-1,3-diamine (~1 mmol, 0.12 mL) with3- ethoxysalicylaldehyde (~2 mmol, 0.330 g) in methanol solution(15 mL) for ~2 h. The resulting solution was then cooled in an ice bath and solid sodium borohydride (3 mmol, 0.120 g) was addedin portion under stirring condition. Afterward, the pH of the solutionwas adjusted with glacial acetic acid (2 mL) and the solutionwas evaporated to dryness using a rotary evaporator (~60 °C).Finally, the remaining semisolid mass was dissolved in distilledwater (15 mL) and extracted with dichloromethane (15 mL) toobtain the desired reduced Schiff base ligand, H2L.
	In methanol for 2h; Reflux;	2.2.1. Synthesis of (2,2-dimethyl-(1,3-propylene))-bis(3-ethoxysalicylideneimine) (H2L1) A clear yellow solution of ligand, H2L2, was synthesized byrefluxing a methanol solution of 2,2dimethyl1,3propanediamine(0.1 ml, 1 mmol) and 3-ethoxysalicylaldehyde (330 mg, 2 mmol) in1:2 ratio for 2 h. It was then used directly for the preparation of thecomplex.
	In methanol for 2h; Reflux;
	In methanol for 1.5h; Reflux;
	In methanol Reflux;
	In methanol for 3h; Reflux;
	at 65℃; for 2h;
	In methanol for 2h; Reflux;	2.2.1. Synthesis of H2L1 [(1,3-propanediyl)bis(iminomethylene)bis(6-methoxyphenol)] A solution of 3-methoxysalicylaldehyde (2 mmol, 0.30 g) and 1,3-propanediamine (1 mmol, 0.11 mL) in 20 mL of methanol wasrefluxed for 2 h to prepare the hexadentate N2O4 donor Schiff baseligand, H2La = N,N’-bis(3-methoxysalicylidene)propane-1,3-diamine.Then the solution was cooled to 0 C and solid sodium borohydride(2.00 mmol, 0.075 g) was gently added to the methanol solution withconstant stirring. The resulting solution was acidified with glacial aceticacid (10 mL) and placed under reduced pressure in a rotary evaporator(~60 C). The residue was dissolved in water (15 mL) and extracted withdichloromethane (15 mL) using a separating funnel. The ligand solutionin dichloromethane was dried using anhydrous sodium acetate andfiltered. Evaporation of the dichloromethane under reduced pressuregave the reduced ligand, H2L1, which was dissolved in methanol. Theligand was not isolated and was used directly for the synthesis of complex1.
	In methanol for 1h; Reflux;

Reference： [1]Majumdar, Dhrubajyoti; Dey, Swapan; Kumari, Annu; Pal, Tapan Kumar; Bankura, Kalipada; Mishra, Dipankar [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2021, vol. 254]
[2]Bankura, Kalipada; Majumdar, Dhrubajyoti; Mishra, Dipankar; Pal, Tapan Kumar; Saini, Reena V.; Tüzün, Burak [Polyhedron, 2021, vol. 210]
[3]Sahraei, Atefeh; Kargar, Hadi; Hakimi, Mohammad; Tahir, Muhammad Nawaz [Transition Metal Chemistry, 2017, vol. 42, # 6, p. 483 - 489]
[4]Sreejith; Mohan, Nithya; Kurup, M.R. Prathapachandra [Polyhedron, 2017, vol. 135, p. 278 - 295]
[5]Ghosh, Kousik; Harms, Klaus; Bauzá, Antonio; Frontera, Antonio; Chattopadhyay, Shouvik [Dalton Transactions, 2018, vol. 47, # 2, p. 331 - 347]
[6]Sarkar, Nandita; Drew, Michael G.B.; Harms, Klaus; Bauzá, Antonio; Frontera, Antonio; Chattopadhyay, Shouvik [CrystEngComm, 2018, vol. 20, # 8, p. 1077 - 1086]
[7]Roy, Sourav; Drew, Michael G. B.; Bauzá, Antonio; Frontera, Antonio; Chattopadhyay, Shouvik [New Journal of Chemistry, 2018, vol. 42, # 8, p. 6062 - 6076]
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43
[ 7328-91-8 ]
[ 84501-28-0 ]
[ 1136209-18-1 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a round-bottomed flask was added 4-tert-butyl-2,6-diformylphenol (1.20 g, 5.80 mmol), NaClO4 (2.81 g, 23.2 mmol), acetic acid (0.66 mL, 11.6 mmol) and methanol (90 mL). This solution was heated to 70 C. whilst stirring, as the solution started to boil, 2,2-dimethyl-1,3-propanediamine (0.70 mL, 5.8 mmol) was added slowly in methanol (30 mL). The yellow reaction mixture was allowed to cool to room temperature, and left stirring for 24 hours, after which a bright orange precipitate was filtered and washed with cold (-78 C.) methanol (1.85 g, 95%). The product was suspended in methanol (180 mL). The suspension was cooled to 0 C. and NaBH4 (2.65 g, 69.9 mmol) was added slowly. As NaBH4 was added, the red-orange suspension turned to a clear solution. Water was added slowly, and the solution turned cloudy. Once precipitate started to form, the mixture was left overnight and H2L11 was filtered off as a white solid (1.21 g, 88%).

Reference： [1]Patent: US2017/210848,2017,A1 .Location in patent: Paragraph 0220; 0265

44
[ 700-44-7 ]
[ 7328-91-8 ]
C₂₁H₂₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol for 2h; Reflux;	2.2. Syntheses of Schiff-base ligands General procedure: The ligand H2L1'(3-methoxysalicylidene)-2,2-dimethyl-1,3-propandiamine was synthesized by adding 3-methoxy-salicylaldehyde(0.609 g, 4 mmol) to a solution of 2,2-dimethyl-1,3-propanediamine (0.204 g, 2 mmol) in ethanol (20 ml). Afterrefluxing for 2 h the solution was left to evaporate slowly at roomtemperature. After 7 days, yellow crystals of H2L1'were isolated.The compound was characterized by using IR, lH NMR spectroscopyand elemental analyses (CHN). Other ligands were produced by thismethod. The X-ray structures of some of the ligands were reportedin previous journal papers [28-30].

Reference： [1]Sahraei, Atefeh; Kargar, Hadi; Hakimi, Mohammad; Tahir, Muhammad Nawaz [Journal of Molecular Structure, 2017, vol. 1149, p. 576 - 584]

45
cerium(III) acetate hydrate [ No CAS ]
[ 7328-91-8 ]
[ 5970-45-6 ]
[ 148063-59-6 ]
C₃₉H₄₂CeN₆O₆Zn₃⁽³⁺⁾*3C₂H₃O₂^(1-) [ No CAS ]