23069-99-0|N-Phenethylformamide| Ambeed

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Quality Control of [ 23069-99-0 ] Purity: 97% SDS Specification

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Product Details of [ 23069-99-0 ]

CAS No. :	23069-99-0
Formula :	C₉H₁₁NO
M.W :	149.19
SMILES Code :	O=CNCCC1=CC=CC=C1
MDL No. :	MFCD00962346
InChI Key :	NOOOMJZHMKSKBF-UHFFFAOYSA-N
Pubchem ID :	140995

Safety of [ 23069-99-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H317-H318-H335-H402
Precautionary Statements:	P261-P264-P270-P271-P272-P273-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P333+P313-P403+P233-P405-P501
Class:	8
UN#:	1760
Packing Group:	Ⅲ

Application In Synthesis of [ 23069-99-0 ]

* 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.

Downstream synthetic route of [ 23069-99-0 ]

[ 23069-99-0 ] Synthesis Path-Downstream 1~35

1
[ 23069-99-0 ]
[ 3230-65-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With PPA; phosphorus pentoxide; at 170℃; for 18h;	Example 1: Preparation of 3,4-dihydroisoquinoline (1, R1, R3, R3', R4, R4', R5, R6, R7, R8=H) To a flame dried 1000 ml three neck round bottomed flask, equipped with an addition funnel, dry argon inlet, magnetic stir bar, thermometer, Dean Stark trap, and heating bath is added 2- phenethylamine (8, R3, R3, R4, R4s, R5, R6, R7, R8=H) (121 gm. , 1.0 mol) and toluene (250 ml). To the addition funnel is added formic acid (46 gm. , 1 mol). The formic acid is added slowly to the stirring reaction solution over 60 minutes and solids form. Once addition is complete the reaction is brought to reflux and water removed via a Dean Stark trap. Once the reaction is complete, the toluene is removed and the product (9, Rl, R3, R3, R4, R4, R5, R6, R7, R8=H) is purified by vacuum distillation. Formamide (9, Rl, R3, R3, R4, R4, R5, R6, R7, R8=H) is then contacted with polyphosphoric acid (747 gm) /phosphorous pentoxide (150 gm), using standard Bischler/Napieralski conditions, at 170C for 18 hours. The reaction is then neutralized with aqueous NaOH, keeping the temperature between 60-80C. Once neutral, the product is extracted with toluene to yield 3,4-dihydroisoquinoline (1, Rl, R3, Ruz R4, R4, R5, R6, R7, R8=H) in 95% yield. Product can be further purified via distillation.
85%		2) Dihydroisoquinoline; Polyphosphoric acid (4.42 kg) was heated to 80 0C under stirring and mixed with P2O5 (0.69 kg). After heating to 170 0C and stirring for 1 h at this temperature N-formyl-N-(2- phenytethyi) amin (1.32 kg, 8.84 moi) was added during 30 min. After stirring for 4 h at 170 0C the reaction was cooled down to 80 0C and carefully mixed with a 20 % solution of potassium hydroxide in water (24.75 kg) in order to result pH 7-8. The crude mixture was extracted at 60 0C with toluene (4 x 4.4 I). From the combined organic phases, which were dried over Na∑SCU, the toluene was removed under vacuum (1 mbar) at 60 0C to give dihydroisoquinone (1.0 kg, 85 % yield, 99.9 % purity via gas chromatography)
78 - 91%Chromat.	With methanesulfonic acid; phosphorus pentoxide; at 115 - 160℃; for 2 - 24h;Neat (no solvent);Product distribution / selectivity;	Examples 18 - 37; Also the following reaction step was varied:(10) (11) (12) with the conditions and results being listed in table 1 below:

76 - 99%Chromat.	With phosphorus pentoxide; at 170 - 200℃; for 0.666667 - 1h;Neat (no solvent);Product distribution / selectivity;	Examples 18 - 37; Also the following reaction step was varied:(10) (11) (12) with the conditions and results being listed in table 1 below:
56.3 g (76.1%)	With PPA; In water;	1.2 Synthesis of 3,4-dihydroisoquinoline 490.0 g (5.00 mol) of polyphosphoric acid were heated to 80 C. until it could be thoroughly mixed with a metal stirrer. Then 84.0 g (0.56 mol) of <strong>[23069-99-0]N-(2-phenylethyl)formamide</strong> from stage 1 were added at 80 C. while stirring and the mixture was heated to 160 C. for 12 hours. After the reaction the mixture was poured onto 1000 ml of iced water and then stirred for 2 hours at room temperature. A pH of 12.0 was established with a 5-molar, aqueous sodium hydroxide solution. The aqueous phase was extracted with methyl tert-butyl ether. The combined organic phases were dried with magnesium sulfate and completely evaporated in a rotary evaporator, resulting in a dark brown oil. The oil was distilled under vacuum (40 mbar/115 C.) and accumulated in the form of a clear, light-brown liquid, which was used in the third stage. Yield: 56.3 g (76.1%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=2.68 (t, 2H); 3.65 (t, 2H); 7.23 (d, 1H); 7.34 (m, 2H); 7.41 (d, 1H); 8.34 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=25.4; 48.0; 127.5; 127.8; 128.9; 131.5; 137.0; 160.7.
56.3 g (76%)	With PPA; In water;	1.2 Synthesis of 3,4-dihydroisoquinoline 490.0 g (5.00 mol) of polyphosphoric acid were heated to 80 C. until it could be thoroughly mixed with a metal stirrer. Then 84.0 g (0.56 mol) of <strong>[23069-99-0]N-(2-phenylethyl)formamide</strong> from stage 1 was added at 80 C. while stirring and the mixture was heated to 160 C. for 12 hours. After the reaction the mixture was poured onto 1000 ml of iced water and then stirred for 2 hours at room temperature. A pH of 12.0 was established with a 5-molar, aqueous sodium hydroxide solution. The aqueous phase was extracted with methyl t-butyl ether. The combined organic phases were dried with magnesium sulfate and completely evaporated in a rotary evaporator, resulting in dark brown oil. The oil was distilled under vacuum (40 mbar/115 C.) and accumulated in the form of a clear, light-brown liquid, which was used in the third stage. Yield: 56.3 g (76%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=2.68 (t, 2H); 3.65 (t, 2H); 7.23 (d, 1H); 7.34 (m, 2H); 7.41 (d, 1H); 8.34 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=25.4; 48.0; 127.5; 127.8; 128.9; 131.5; 137.0; 160.7.
5 g	With polyphosphoric acid; at 160℃;	2-Phenylethylamine (30.0 g, 0.248 mol) and ethyl formate were heated at reflux for 2 days. Removal of excess ethyl formate under vacuum gave the <strong>[23069-99-0]N-phenethylformamide</strong> in quantitative yield (37.0 g) as a colorless oil. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 8.10 (1H, s, CHO); 7.29 (2H, t, J = 7.2, H Ar); 7.24-7.13 (3H, m, H Ar); 6.7-6.2 (1H, br. s, NH); 3.50 (2H, t, J = 7.0, CH2); 2.81 (2H, t, J =7.0, CH2). 13C NMR spectrum (CDCl3), δ, ppm: 161.4; 138.6; 128.8; 128.7; 126.6; 39.2; 35.5. Crude 2-phenylethylamine (7.0 g, 0.47 mol) and polyphosphoric acid (20 ml) were heated at 160C overnight. The reaction mixture was cooled to room temperature and made basic with 5 M NaOH; a white precipitate formed. The precipitate was filtered off, and the filtrate was extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to yield compound 2 (5.0 g, 81%) as a pale-yellow oil. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 8.31 (1H, t, J = 2.3, H Ar); 7.36-7.20 (3H, m, H Ar); 7.19-7.05 (1H, m, H Ar); 3.83-3.70 (2H, m, CH2); 2.81-2.69 (2H, m, CH2). 13C NMR spectrum (CDCl3), δ, ppm: 160.7; 136.7; 131.7; 128.9; 127.8; 127.6; 127.5; 47.8; 25.4.

References: [1]Journal of Heterocyclic Chemistry,2005,vol. 42,p. 647 - 659.
[2]Patent: WO2005/47264,2005,A1 .Location in patent: Page/Page column 14-15.
[3]Organic and Biomolecular Chemistry,2003,vol. 1,p. 3038 - 3047.
[4]Patent: WO2006/134143,2006,A1 .Location in patent: Page/Page column 26.
[5]Chemische Berichte,1930,vol. 63,p. 134,136.
[6]Journal of the American Pharmaceutical Association (1912),1958,vol. 47,p. 353.
[7]Journal of Medicinal Chemistry,1983,vol. 26,p. 1426 - 1433.
[8]Gazzetta Chimica Italiana,1984,vol. 114,p. 35 - 40.
[9]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1991 - 1996.
[10]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 956 - 962.
[11]Tetrahedron Asymmetry,2008,vol. 19,p. 2784 - 2788.
[12]Patent: WO2006/134143,2006,A1 .Location in patent: Page/Page column 28.
[13]Patent: WO2006/134143,2006,A1 .Location in patent: Page/Page column 28.
[14]Patent: US2011/56508,2011,A1 .
[15]Patent: US2011/146005,2011,A1 .
[16]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 1214 - 1219.
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 1214 - 1219,6.

2
[ 23069-99-0 ]
[ 589-08-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	With lithium aluminium tetrahydride; In tetrahydrofuran;Reflux;	Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of LiAlH4 (868 mg, 22.84 mmol, 1.50 equiv) in tetrahydrofuran (70 mL). This was followed by the addition of a solution of <strong>[23069-99-0]N-phenethylformamide</strong> (2.27 g, 15.23 mmol, 1.00 equiv) intetrahydrofuran (50 mL) dropwise with stirring while the resulting solution maintained reflux. The resulting solution was stirred overnight at reflux in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 4x30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column withdichloromethane/methanol (100:1). This resulted in 1.36 g (34%) of N-methyl-2- phenylethanamine as yellow oil.

References: [1]Patent: WO2011/28947,2011,A2 .Location in patent: Page/Page column 133-134.
[2]Journal of the American Chemical Society,1958,vol. 80,p. 4588,4592.
[3]Journal of the Chemical Society,1929,p. 1798.

3
[ 140-29-4 ]
[ 60100-09-6 ]
[ 23069-99-0 ]

Yield	Reaction Conditions	Operation in experiment
14%Spectr.	With nickel; hydrogen; In tert-butyl alcohol; at 70℃; under 760.051 Torr; for 7h;	General procedure: To a suspension of 0.4 g (0.012 mol) of sodium borohydride in 20 mL of piperidine 6a at 30C was added 0.8 g (0.006 mol) of anhydrous nickel(II) chloride. The mixture was heated to 60C to produce black colloid solution of a catalyst. Butyronitrile (6.9 g, 0.1 mol) was added to the resulting catalyst, and hydrogen was passed at 70C for 14 h. After cooling, 1 mL of water was added to the mixture to accelerate the catalyst coagulation. The precipitate was filtered off, the filtrate was analyzed. N-n-Butylidene-n-butylamine (5a), content 8%. Mass spectrum, m/e (Irel, %): 128.8 (13) [M + 2], 127.8 (100) [M + 1], 125.9 (4), 111.9 (16), 85.1 (8), 84.1 (53), 83.2 (9), 70.2 (16), 57.2 (26), 56.2 (30), 55.2 (10), 42.1 (50), 41.2 (34), 40.2 (3). N-n-Butylpiperidin (7a), content 19%. Mass spectrum, m/e (Irel,%): 141.9 (6) [M + 1], 140.7 (2) [M], 139.9 (5), 98.9 (6), 98.0 (100), 70.0 (10), 42.1 (7). N-1-Butyl-1-idenpiperidin (8a), content 39%. Mass spectrum, m/e (Irel, %): 139.9 (4) [M + 1], 138.8 (20) [M], 138.0 (7), 125.0 (9), 124.0 (100), 110.0 (8), 96.0 (4), 94.0 (5), 68.0 (20), 42.2 (6), 41.2 (9). N-1-Butyl-1-idendi-nbutylamine (9), content 31%. Mass spectrum, m/e (Irel, %): 183.0 (12) [M], 182.0 (100), 181.1 (9), 152.2 (6), 124.0 (5), 41.2 (3).

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 520,522,523.
Chem.Abstr.,1951,p. 5640.
[2]Russian Journal of General Chemistry,2016,vol. 86,p. 798 - 805.
Zh. Obshch. Khim.,2016,vol. 86,p. 609 - 616,8.

4
[ 64-18-6 ]
[ 64-04-0 ]
[ 23069-99-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sulfated tungstate; at 70℃; for 0.166667h;Neat (no solvent);	General procedure for N-formylation reaction: A stirred mixture of amine (1 mmol), formic acid (0.4 g, 1.2 mmol), and sulfated tungstate (10 wt %) was heated in an oil bath at 70 C and the progress of the reaction was monitored by TLC. The reaction mixture was worked up as follows. It was cooled to rt, diluted by adding ethyl acetate (10 ml) with stirring and the insoluble catalyst was recovered by filtration and washed with ethyl acetate (3 × 5 ml). Combined organic layer (filtrate and washings) was washed with H2O (2 × 10 ml), dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to get product as residue in almost pure form.
15%	With pyridine; diisopropyl-carbodiimide; at 20℃; for 72h;	2-Phenethylamine (1 mmol, 125 μL) was dissolved in pyridine (0.5 mL) and a mixture of formic acid (4 mmol, 150 μL) and diisopropylcarbodiimide (DIPCD, 4 mmol, 600 μL) was added to the solution. The resulting mixture was stirred for 72 h at room temperature. The products were purified by silica gel flash column chromatography (CH2Cl2; CH2Cl2/acetone 9:1, 5:5; acetone; acetone/MeOH 5:5) and then reversed-phase HPLC (XBridge Prep Phenyl OBD, 16% MeOH) to give 3 (22.7 mg, 15.0% yield). Compound 3 was obtained a set of rotational isomers (3a and 3b). The molar ratio of 3a to 3b was 5.7 to 1. Compound 3a: 1H NMR (CDCl3, 270 MHz) δ 8.03 (1H, s), δ 7.07-7.27 (5H, m), δ 5.61 (1H, br s), δ 3.50 (2H, q, 7.2), δ 2.76 (2H, t, 7.0). Compound 3b: δ 7.83 (1H, d, 11.9), δ 7.07-7.27 (5H, m), δ 3.39 (2H, q, 6.8), δ 2.76 (2H, t, 7.0); ESIMS m/z 172 [M+Na]+; HRESIMS m/z 172.0738 [M+Na]+ (calcd for C9H11N1NaO1, 172.0746).
	In toluene; for 1h;Heating / reflux;	Example 1: Preparation of 3,4-dihydroisoquinoline (1, R1, R3, R3', R4, R4', R5, R6, R7, R8=H) To a flame dried 1000 ml three neck round bottomed flask, equipped with an addition funnel, dry argon inlet, magnetic stir bar, thermometer, Dean Stark trap, and heating bath is added 2- phenethylamine (8, R3, R3, R4, R4s, R5, R6, R7, R8=H) (121 gm. , 1.0 mol) and toluene (250 ml). To the addition funnel is added formic acid (46 gm. , 1 mol). The formic acid is added slowly to the stirring reaction solution over 60 minutes and solids form. Once addition is complete the reaction is brought to reflux and water removed via a Dean Stark trap. Once the reaction is complete, the toluene is removed and the product (9, Rl, R3, R3, R4, R4, R5, R6, R7, R8=H) is purified by vacuum distillation. Formamide (9, Rl, R3, R3, R4, R4, R5, R6, R7, R8=H) is then contacted with polyphosphoric acid (747 gm) /phosphorous pentoxide (150 gm), using standard Bischler/Napieralski conditions, at 170C for 18 hours. The reaction is then neutralized with aqueous NaOH, keeping the temperature between 60-80C. Once neutral, the product is extracted with toluene to yield 3,4-dihydroisoquinoline (1, Rl, R3, Ruz R4, R4, R5, R6, R7, R8=H) in 95% yield. Product can be further purified via distillation.

References: [1]Chemical Research in Toxicology,2020,vol. 33,p. 955 - 966.
[2]Tetrahedron Letters,2012,vol. 53,p. 3259 - 3263.
[3]European Journal of Organic Chemistry,2021,vol. 2021,p. 4477 - 4484.
[4]Tetrahedron,2011,vol. 67,p. 6649 - 6653.
[5]Synthesis,1987,p. 1031 - 1032.
[6]Journal of Medicinal Chemistry,1983,vol. 26,p. 1426 - 1433.
[7]Gazzetta Chimica Italiana,1984,vol. 114,p. 35 - 40.
[8]Chemische Berichte,1929,vol. 62,p. 323.
[9]Patent: WO2005/47264,2005,A1 .Location in patent: Page/Page column 14-15.
[10]Organic Letters,2011,vol. 13,p. 106 - 109.
[11]Journal of Medicinal Chemistry,2019,vol. 62,p. 589 - 603.

5
[ 50-00-0 ]
[ 23069-99-0 ]
[ 1699-52-1 ]

Yield	Reaction Conditions	Operation in experiment
97 - 99%Chromat.	With trifluoroacetic acid; for 4.5h;Neat (no solvent); Heating / reflux;Product distribution / selectivity;	Examples 38 to 56; The following reaction step was also object ob further experiments, which are summarized in table 2 below:
95%Chromat.	With methanesulfonic acid; In 1,2-dichloro-ethane; for 4.5h;Heating / reflux;Product distribution / selectivity;	Examples 38 to 56; The following reaction step was also object ob further experiments, which are summarized in table 2 below:
	With formic acid; at 67℃; for 7.5h;	75 parts by mass of formyl phenethylamine was added to 267 parts by mass of formic acid, 20 parts by mass of paraformaldehyde was added, the temperature was raised to 67 C, and the reaction was carried out for 7.5 hours. The concentrated formic acid was removed to obtain a crude product.

References: [1]Synthesis,1987,p. 1031 - 1032.
[2]Patent: WO2006/134143,2006,A1 .Location in patent: Page/Page column 29.
[3]Patent: WO2006/134143,2006,A1 .Location in patent: Page/Page column 29.
[4]Patent: CN106749014,2017,A .Location in patent: Paragraph 0022; 0026; 0028; 0030; 0034; 0038.

6
[ 23069-99-0 ]
[ 555-16-8 ]
[ 119492-63-6 ]

References: [1]Synthesis,1987,p. 1031 - 1032.

7
[ 64-04-0 ]
[ 146039-03-4 ]
[ 23069-99-0 ]

References: [1]Synthesis,1992,p. 1058 - 1060.

8
[ 64-04-0 ]
[ 109-94-4 ]
[ 23069-99-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	at 50℃;Inert atmosphere;	Into a 100-mL 3 -necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-phenylethanamine (1.9 g, 15.70 mmol, 1.00 equiv). This was followed by the addition of ethyl formate (5 g, 67.57 mmol, 4.30 equiv) dropwise with stirring. The resulting solution was stirred overnight at 50C. The resulting solution was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (70:1). This resulted in 2.27 g (97%) of N-phenethylformamide as yellow oil.LC-MS: (ES, m/z): 150 [M+H]+
	at 50℃; for 1.5h;	Under nitrogen at room temperature, to (2-phenylethyl)amine (20 g) was added dropwise ethyl formate (49.6 g), and the mixture was stirred at 50 C. for 1.5 hours.The resulting mixture was evaporated and dried in vacuo to give (2-phenylethyl)formamide (25 mg). (-)ESI-MS (m/z): 148 (M-H)-
	for 3h;Reflux;	General procedure: The respective amine (4 mmol, 1 eq) and ethyl formate (4.4 mmol, 1.1 eq) are refluxed for 3 h. After 5 min of evaporation of the volatile reaction products by opening the reaction apparatus, 10 ml of dry DCM are added as well as PPh3 (4.8 mmol, 1.2 eq), NEt3 (4 mmol, 1 eq) and CCl4 (4 mmol,1 eq). The apparatus is charged with argon and the mixture refluxed for 4 h. After cooling to room temperature, a premixed solution (30 min) of 10 ml dry methanol, the respective 2-aminopyridine (2 mmol, 0.5 eq), aldehyde (2 mmol, 0.5 eq) and glacial acetic acid (6 mmol, 1.5 eq) is added. After 48h at 40 C the formation of imidazo[1,2-a]pyridine is controlled by TLC and several grams of silica gel are added to the reaction mixture. After evaporating to dryness on a rotavapor, the loaded silica gel is worked up by column chromatography (hexane/ethyl acetate 10:1, 5:1, 3:1 and 1:1) to furnish the desired product.

	for 48h;Reflux;	2-Phenylethylamine (30.0 g, 0.248 mol) and ethyl formate were heated at reflux for 2 days. Removal of excess ethyl formate under vacuum gave the N-phenethylformamide in quantitative yield (37.0 g) as a colorless oil. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 8.10 (1H, s, CHO); 7.29 (2H, t, J = 7.2, H Ar); 7.24-7.13 (3H, m, H Ar); 6.7-6.2 (1H, br. s, NH); 3.50 (2H, t, J = 7.0, CH2); 2.81 (2H, t, J =7.0, CH2). 13C NMR spectrum (CDCl3), δ, ppm: 161.4; 138.6; 128.8; 128.7; 126.6; 39.2; 35.5.
	at 20℃; for 4 - 6h;Heating / reflux;	Ethyl formate (120 mmol) was added dropwise to phenylalkylamine (40 mmol) at room temperature and the resulting mixture was refluxed for 4- 6 h. The excess ethyl formate was removed under reduced pressure to yield the corresponding phenylakylformamide as an oil.
	at 20 - 50℃; for 1.5h;	Preparation 1 Under nitrogen at room temperature, to (2-phenylethyl)- amine (20 g) was added dropwise ethyl formate (49.6 g), and the mixture was stirred at 50C for 1.5 hours. The resulting mixture was evaporated and dried in vacuo to give (2- phenylethyl) formamide (25 g). (-) ESI-MS m/z: 148 (M-H)-

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 3038 - 3047.
[2]Chemical Communications,2017,vol. 53,p. 2382 - 2385.
[3]Organic and Biomolecular Chemistry,2018,vol. 16,p. 5332 - 5342.
[4]Patent: WO2011/28947,2011,A2 .Location in patent: Page/Page column 133.
[5]Journal of Medicinal Chemistry,2008,vol. 51,p. 7820 - 7826.
[6]ChemBioChem,2020,vol. 21,p. 3608 - 3617.
[7]Organic Magnetic Resonance,1981,vol. 15,p. 7 - 12.
[8]Patent: US2004/106653,2004,A1 .Location in patent: Page/Page column 44.
[9]Pharmazie,2015,vol. 70,p. 507 - 510.
[10]Journal of Medicinal Chemistry,2017,vol. 60,p. 7199 - 7205.
[11]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 1214 - 1219.
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 1214 - 1219,6.
[12]Patent: WO2008/128189,2008,A1 .Location in patent: Page/Page column 26.
[13]Patent: WO2005/110981,2005,A1 .Location in patent: Page/Page column 15.
[14]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4814 - 4819.
[15]Green Chemistry,2019,vol. 21,p. 3263 - 3266.
[16]Organic Letters,2021,vol. 23,p. 5197 - 5202.

9
[ 23069-99-0 ]
[ 106-96-7 ]
C₁₂H₁₃NO [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 2741 - 2743.

10
[ 23069-99-0 ]
[ 84500-68-5 ]

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 3038 - 3047.

11
[ 23069-99-0 ]
[ 76467-31-7 ]

References: [1]Journal of Organic Chemistry,1981,vol. <6> 46,p. 1224 - 1227.

12
[ 23069-99-0 ]
[ 76467-32-8 ]

References: [1]Journal of Organic Chemistry,1981,vol. <6> 46,p. 1224 - 1227.

13
[ 23069-99-0 ]
[ 76467-36-2 ]

References: [1]Journal of Organic Chemistry,1981,vol. <6> 46,p. 1224 - 1227.

14
[ 23069-99-0 ]
[ 76467-33-9 ]

References: [1]Journal of Organic Chemistry,1981,vol. <6> 46,p. 1224 - 1227.

15
[ 23069-99-0 ]
[ 119-65-3 ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 1212,1215.
[2]Chemische Berichte,1930,vol. 63,p. 134,136.

16
[ 23069-99-0 ]
[ 50893-11-3 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 4588,4592.

17
[ 23069-99-0 ]
[ 14130-48-4 ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 1212,1215.
[2]Journal of the American Chemical Society,1957,vol. 79,p. 1212,1215.

18
[ 23069-99-0 ]
[ 111413-37-7 ]