Name: 3-Formylchromone
Brand: Ambeed
SKU: A185556
Rating: 4.0 (180 reviews)

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Quality Control of 3-Formylchromone Purity: 97% SDS Specification

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Product Details of 3-Formylchromone

CAS No. :	17422-74-1
Formula :	C₁₀H₆O₃
M.W :	174.15
SMILES Code :	O=CC1=COC2=CC=CC=C2C1=O
English Name :	4-Oxo-4H-chromene-3-carbaldehyde
MDL No. :	MFCD00014667
InChI Key :	FSMYWBQIMDSGQP-UHFFFAOYSA-N
Pubchem ID :	87112

Safety of 3-Formylchromone

GHS Pictogram:
Signal Word:
Hazard Statements:
Precautionary Statements:
Class:
UN#:
Packing Group:

Application In Synthesis of 3-Formylchromone

* 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 [ 17422-74-1 ]

[ 17422-74-1 ] Synthesis Path-Downstream 1~63

1
[ 14246-53-8 ]
[ 17422-74-1 ]
[ 77420-35-0 ]

Yield	Reaction Conditions	Operation in experiment
26%	With sodium acetate In acetic anhydride steam-bath;

References: [1]Jones, Winton D. [Journal of the Chemical Society. Perkin transactions I, 1981, p. 344 - 348].

2
[ 343868-71-3 ]
[ 17422-74-1 ]
[ 78831-27-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	In acetic acid for 2h; Heating;

References: [1]Hass, Georges; Stanton, James L.; Sprecher, Andreas von; Wenk, Paul [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 607 - 612].

3
[ 17422-74-1 ]
[ 1124-16-9 ]
[ 78831-28-4 ]

References: [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 607 - 612.

4
[ 17422-74-1 ]
[ 19790-96-6 ]
[ 78831-29-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	In acetic acid for 4h; Heating;

References: [1]Hass, Georges; Stanton, James L.; Sprecher, Andreas von; Wenk, Paul [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 607 - 612].

5
[ 553-53-7 ]
[ 17422-74-1 ]
[ 285986-31-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid In ethanol Heating;
90%	With acetic acid In ethanol for 6h; Heating;
56%	In ethanol

References: [1]Tsao; Van; Sun; Lyu [Russian Journal of General Chemistry, 2001, vol. 71, # 5, p. 767 - 769].
[2]Cao; Wang [Chemistry of Heterocyclic Compounds, 2003, vol. 39, # 8, p. 1072 - 1075].
[3]Location in patent: scheme or table Khan, Khalid M.; Ambreen, Nida; Mughal, Uzma Rasool; Jalil, Saima; Perveen, Shahnaz; Choudhary, M. Iqbal [European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4058 - 4064].

6
[ 17422-74-1 ]
[ 50743-17-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydroxylamine hydrochloride In acetonitrile for 2h; Heating;
	With formic acid; hydroxylamine hydrochloride; sodium formate In water	10 4-Oxo-4H-1-Benzopyran-3-carbonitrile EXAMPLE 10 SPC21 4-Oxo-4H-1-Benzopyran-3-carbonitrile A mixture of 26.1 g. (0.15 mole) of 4-oxo-4H-1-benzopyran-3-carboxaldehyde, 13.1 g. (0.19 mole) of hydroxylamine hydrochloride, 18.4 g. (0.27 mole) of sodium formate and 250 ml of 99% formic acid was heated with stirring at reflux for 21/2 hours. Water was added to 1-liter volume. The separated solid was filtered from the cooled mixture, washed well with water and dried to give 13 g. (51%) of crude nitrile melting at 138°-145°C. Recrystallization from ethylacetate gave pure, white crystals melting at 174°-176°. Anal. Calcd for C10 H5 NO2: C, 70.17; H, 2.94; N, 8.18. Found: C, 70.18; H, 3.05; N, 8.22.
	With ammonium azide; sulfuric acid In ethanol at 30℃;	1H-Tetrazoles 2a-z; General Procedure General procedure: (CAUTION Sodium azide can explode on heating and is highlytoxic. Contact of metal azides with acids liberates highly toxicand explosive hydrazoic acid.)NH4N3 (0.5 mmol) and H2SO4 (0.5 mmol) were added sequentiallyto a round-bottomed flask containing the appropriatealdehyde (0.5 mmol) in EtOH (1 mL), and the resulting mixturewas stirred at r.t. for 10 min. A solution of NaN3 (0.5 mmol) inH2O (1 mL) was then added, and the resulting mixture wasstirred for another 2 h at 80 °C. When the starting material hadbeen consumed, the mixture was cooled to r.t. and ice-cold H2Owas added to give a solid precipitate. The precipitate was collectedand washed with 20% CH2Cl2-hexane to give the pureproduct.

References: [1]Jagath Reddy; Latha; Thirupathaiah; Srinivasa Rao [Organic Preparations and Procedures International, 2004, vol. 36, # 3, p. 287 - 289].
[2]Current Patent Assignee: WARNER LAMBERT LLC - US3937837, 1976, A.
[3]Singh, Rajeev; Ahmed, Naseem [Synlett, 2024, vol. 36, # 8, p. 1003 - 1008].

7
[ 654-62-6 ]
[ 17422-74-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In methanol Heating;

References: [1]Puccetti, Luca; Fasolis, Giuseppe; Vullo, Daniela; Chohan, Zahid H.; Scozzafava, Andrea; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 3096 - 3101].

8
[ 19933-22-3 ]
[ 17422-74-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium acetate In acetic acid for 0.5h; Heating;

References: [1]Khodairy [Journal of the Chinese Chemical Society, 2007, vol. 54, # 1, p. 93 - 102].

9
[ 75-77-4 ]
[ 53681-51-9 ]
[ 17422-74-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide Heating;

References: [1]Ryabukhin, Sergey V.; Plaskon, Andrey S.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2007, # 12, p. 1861 - 1871].

10
[ 75-77-4 ]
[ 17422-74-1 ]
[ 88786-11-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide Heating;

References: [1]Ryabukhin, Sergey V.; Plaskon, Andrey S.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2007, # 12, p. 1861 - 1871].

11
[ 542-02-9 ]
[ 17422-74-1 ]
[ 1020416-75-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating;

References: [1]Ryabukhin, Sergey V.; Plaskon, Andrey S.; Volochnyuk, Dmitriy M.; Pipko, Sergey E.; Tolmachev, Andrey A. [Heterocycles, 2008, vol. 75, # 3, p. 583 - 597].

12
[ 44565-47-1 ]
[ 17422-74-1 ]
[ 949679-99-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; for 15h;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

13
[ 51221-45-5 ]
[ 17422-74-1 ]
[ 949218-80-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: (4-methylthiazol-2-yl)methanamine; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

14
[ 51221-45-5 ]
[ 17422-74-1 ]
[ 1040257-39-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

15
[ 6971-44-4 ]
[ 17422-74-1 ]
[ 1017219-11-2 ]

References: [1]Tetrahedron,2008,vol. 64,p. 5933 - 5943.

16
[ 923156-44-9 ]
[ 17422-74-1 ]
[ 924122-11-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: C₆H₁₀N₄; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

17
[ 885461-42-7 ]
[ 17422-74-1 ]
[ 924155-83-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: C₈H₁₄N₄; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

18
[ 900640-73-5 ]
[ 17422-74-1 ]
[ 875419-43-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: C₁₁H₁₂ClN₃O; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

19
[ 876316-38-0 ]
[ 17422-74-1 ]
[ 1040257-27-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 2-(1-pyrrolidino)-4-(aminomethyl)pyridine; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

20
[ 876316-38-0 ]
[ 17422-74-1 ]
[ CAS Unavailable ]
[ 1040257-27-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(1-pyrrolidino)-4-(aminomethyl)pyridine; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

21
[ 98997-01-4 ]
[ 17422-74-1 ]
[ 1031141-15-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 2-(methylaminomethyl)benzimidazole; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

22
[ 24152-95-2 ]
[ 17422-74-1 ]
[ 949680-17-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 2-amino-1-(pyrrolidin-1-yl)ethan-1-one; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

23
[ 17422-74-1 ]
[ 91981-59-8 ]
[ 875158-55-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 3-Formylchromone; 1-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethanamine With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

24
[ 17422-74-1 ]
[ 20028-40-4 ]
[ 949304-63-6 ]

References: [1]Tetrahedron,2008,vol. 64,p. 5933 - 5943.

25
[ 17422-74-1 ]
[ 17681-30-0 ]
[ 873208-86-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 3-Formylchromone; 1-(benzo[d]thiazol-2-yl)-N-methylmethanamine With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Tetrahedron, 2008, vol. 64, # 25, p. 5933 - 5943].

26
[ 25706-29-0 ]
[ 17422-74-1 ]
[ 1042977-05-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: 6-amino-2-methylthiobenzo[4,5-d]thiazole; 3-Formylchromone With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Stage #2: In water at 20℃; for 1h; sonication; Further stages.;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Gavrilenko, Konstantin S.; Shivanyuk, Alexander N.; Tolmachev, Andrey A. [Journal of Organic Chemistry, 2008, vol. 73, # 15, p. 6010 - 6013].

27
[ 848369-52-8 ]
[ 17422-74-1 ]
[ 941028-33-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With chloro-trimethyl-silane In N,N-dimethyl-formamide for 18h; Heating;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2008, # 7, p. 1069 - 1077].

28
[ 730949-85-6 ]
[ 17422-74-1 ]
[ 924469-36-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With chloro-trimethyl-silane In N,N-dimethyl-formamide for 20h; Heating;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2008, # 7, p. 1069 - 1077].

29
[ 19062-52-3 ]
[ 17422-74-1 ]
[ 857041-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro-trimethyl-silane In N,N-dimethyl-formamide for 30h; Heating;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2008, # 7, p. 1069 - 1077].

30
[ 17422-74-1 ]
[ 30750-23-3 ]
[ 872103-16-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; for 12h;

References: [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2008, # 7, p. 1069 - 1077].

31
[ 3996-29-0 ]
[ 17422-74-1 ]
[ 1135238-34-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium acetate In toluene at 60℃; for 8h;

References: [1]Location in patent: experimental part Lácová, Margita; Gašparová, Renata; Koiš, Pavol; Boháč, Andrej; El-Shaaer, Hafez M. [Tetrahedron, 2010, vol. 66, # 6, p. 1410 - 1419].

32
[ 28710-97-6 ]
[ 17422-74-1 ]
[ 1253038-69-5 ]

References: [1]Synthesis,2010,p. 2749 - 2758.

33
[ 119-65-3 ]
[ 17422-74-1 ]
[ 2632-10-2 ]
[ 1286733-66-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

References: [1]Naskar, Subhendu; Banerjee, Maitreyee; Hazra, Abhijit; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Sahu, Krishnendu B.; Saha, Pritam; Banerjee, Sukdeb; Mondal, Nirup B. [Tetrahedron Letters, 2011, vol. 52, # 13, p. 1527 - 1531].

34
[ 17422-74-1 ]
[ 159326-69-9 ]
[ 1623055-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(II) choride dihydrate; sodium acetate In dimethyl sulfoxide at 120℃; for 2h;

References: [1]Xiang, Haoyue; Chen, Yanhong; He, Qian; Xie, Yuyuan; Yang, Chunhao [RSC Advances, 2013, vol. 3, # 17, p. 5807 - 5810].

35
[ 64-17-5 ]
[ 80-35-3 ]
[ 17422-74-1 ]
[ 1449215-89-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With toluene-4-sulfonic acid Heating;	4.1. General method for the synthesis of compounds 3ae3e and4a-4f General procedure: A solution of 0.001 M 6-(un)substituted 3-formylchromone in10 mL ethanol was stirred with heating until dissolved. Catalytic amount of p-toluenesulfonic acid (p-TsOH) was added (for compounds3a-3e) followed by the addition of equimolar solution of appropriate sulfonamide in 10 mL of ethanol. The reaction mixture was refluxed for 3.5 h and kept overnight. Solid product was obtainedby filtration and purified by recrystallization from a mixtureof hot ethanol and acetone (1:1).

References: [1]Al-Rashida, Mariya; Raza, Rabia; Abbas, Ghulam; Shah, Muhammad Shakil; Kostakis, George E.; Lecka, Joanna; Sev́igny, Jean; Muddassar, Muhammad; Papatriantafyllopoulou, Constantina; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2013, vol. 66, p. 438 - 449].

36
[ 73870-25-4 ]
[ 17422-74-1 ]
[ 1550910-00-3 ]

Yield	Reaction Conditions	Operation in experiment
34%	Stage #1: (pyridin-4-ylmethyl)triphenylphosphonium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 3-Formylchromone In tetrahydrofuran at 20℃; for 20h;	General procedure for the synthesis of [2-(2H-chromen-3-yl)vinyl]pyridines (5a, 5b, 6a, 6b, 7a, 7b, 8a, 9a) and 3-[2-(pyridinyl)vinyl]-4H-chromen-4-ones (11a, 11b, 12a, 12b, 13a, 13b) General procedure: Potassium tert-butoxide (20 mmol) was added to a stirred suspension of the appropriate pyridilmethyltriphenylphosphonium chloride (2, 3 or 4) (10 mmol) in dry THF (63 mL). After stirring for 10min at room temperature, a solution of the appropriate 2H-chromene-3-carbaldehyde (1a or 1b) (10 mmol) or 4-oxo-4H-chromene-3-carbaldehyde (10a or 10b) (10 mmol) in dry THF (43 mL) was added dropwise. The resulting mixture was stirred at room temperature for 20 h. After this period, water was added, THF was removed under reduced pressure and the residue was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulphate, filtered and evaporated to dryness. In the cases of 3-[2-(2H-chromen-3-yl)vinyl]pyridines (6a, 8a) and 4-[2-(2H-chromen-3-yl)vinyl]pyridines (7a, 9a), the obtained mixtures of (E) and (Z) isomers were separated by column chromatography on silica gel, eluting with ethyl acetate/light petroleum (1:1). The (Z) isomer was eluted at first. For the other compounds only one isomer was purified eluting with ethyl acetate/light petroleum (1:1) (6b, 12b), (1:2) (5a, 11a), or (1:3) (5b, 7b, 11b, 12a, 13a, 13b). Compounds 11a, 11b, 13a and 13b were crystallized as hydrochlorides.

References: [1]Conti, Cinzia; Proietti Monaco, Luca; Desideri, Nicoletta [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1201 - 1207].

37
[ 17422-74-1 ]
[ 4865-84-3 ]
3-(((E)-2-benzo[d]isoxazol-3-yl)vinyl)-4H-chromen-4-one [ No CAS ]

References: [1]Indian Journal of Heterocyclic Chemistry,2012,vol. 22,p. 53 - 60.

38
[ 93-67-4 ]
[ 17422-74-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 5-chloro-2-phenoxyaniline; 3-Formylchromone In methanol for 2h; Stage #2: In methanol for 3 - 4h; Reflux;	3-[(2-Phenoxy-phenylimino)methyl]chromen-4-one (L1) and 3-[(5-chloro-2-phenoxy-phenylimino)methyl]chromen-4-one (L2) General procedure: 5-chloro-2-phenoxy-phenylamine (0.66 g, 3mmol)/2-phenoxy-phenylamine (0.55 g, 3 mmol) dissolvedin methanol (30 mL) was added drop-wise to a methanolic solution of 3-formyl chromone (0.522 g, 3 mmol) with continous stirring for 2 h. The reaction mixture was then refluxed for 3-4 h. The feasibility of reaction was checked frequentlywith TLC. The coloured solid product so obtained was recrystallized in hot methanol then filter the mixture and dried to get pure product.

References: [1]Devi, Jai; Yadav, Manju [Asian Journal of Chemistry, 2017, vol. 29, # 3, p. 551 - 554].

39
[ 38191-33-2 ]
[ 17422-74-1 ]
[ 2101950-70-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	In ethanol	2 4.1.2. General procedures for the preparation of compounds s1-23 General procedure: One equivalent of aldehyde derivatives was reacted with one equivalent of different substituted phenylamine derivatives in ethanol for 3-6 h at room temperature and the solvent was removed under reduced pressure. The resulting crude compounds were washed with cold water and recrystallized by using appropriate solvents to afford the target products s1-23

References: [1]Li, Fan; Wu, Jia-Jia; Wang, Jin; Yang, Xue-Lian; Cai, Pei; Liu, Qiao-Hong; Kong, Ling-Yi; Wang, Xiao-Bing [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3815 - 3826].

40
[ 25706-29-0 ]
[ 17422-74-1 ]
[ 210094-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In toluene for 1h; Heating; Yield given;

References: [1]El-Shaaer, Hafez M.; Foltinova, Pavlina; Lacova, Margita; Chovancova, Jarmila; Stankovicova, Henrieta [Il Farmaco, 1998, vol. 53, # 3, p. 224 - 232].

41
[ 13612-34-5 ]
[ 17422-74-1 ]
(E)-3-(2,5-dimethylstyryl)-4H-chromen-4-one [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 5984 - 5987.

42
[ 17422-74-1 ]
[ 145689-41-4 ]
(E)-3-(2,3-difluorostyryl)-4H-chromen-4-one [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 5984 - 5987.

43
[ 17422-74-1 ]
[ 653-11-2 ]
[ 3047367-72-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-Formylchromone In ethyl acetate at 20℃; for 0.0833333h; Stage #2: 2,3,5,6-tetrafluorophenylhydrazine In ethyl acetate for 48h; Reflux;	3.2. Synthesis of Hydrazine and Hydrazide Derivatives of 3-Formylchromone General procedure: 3-Formylchromone (50 mg, 0.287 mmol) was dissolved in ethyl acetate (30 mL) at roomtemperature. The temperature was raised to reflux temperature and mixture was stirred until the3-formylchromone was fully dissolved. After 5 min, a suitable amount (1 molar equivalent) ofsubstituted aromatic hydrazine or hydrazide was slowly added (dissolved just before addition in ethylacetate). Substances were mixed and heated under reflux for 48 h. The obtained precipitates werefiltered and air-dried. Resulting substances was recrystallized from 50:50 acetone/ethanol.

References: [1]SLomiak, Krzysztof; Lazarenkow, Andrzej; Chęcińska, Lilianna; Kusz, Joachim; Ochocki, Justyn; Nawrot-Modranka, Jolanta [Molecules, 2018, vol. 23, # 8].

44
[ 17422-74-1 ]
[ 80025-72-5 ]
[ 3047367-74-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 3-Formylchromone In ethyl acetate at 20℃; for 0.0833333h; Stage #2: (2,4,6-trifluorophenyl)hydrazine In ethyl acetate for 48h; Reflux;	3.2. Synthesis of Hydrazine and Hydrazide Derivatives of 3-Formylchromone General procedure: 3-Formylchromone (50 mg, 0.287 mmol) was dissolved in ethyl acetate (30 mL) at roomtemperature. The temperature was raised to reflux temperature and mixture was stirred until the3-formylchromone was fully dissolved. After 5 min, a suitable amount (1 molar equivalent) ofsubstituted aromatic hydrazine or hydrazide was slowly added (dissolved just before addition in ethylacetate). Substances were mixed and heated under reflux for 48 h. The obtained precipitates werefiltered and air-dried. Resulting substances was recrystallized from 50:50 acetone/ethanol.

References: [1]SLomiak, Krzysztof; Lazarenkow, Andrzej; Chęcińska, Lilianna; Kusz, Joachim; Ochocki, Justyn; Nawrot-Modranka, Jolanta [Molecules, 2018, vol. 23, # 8].

45
[ 17422-74-1 ]
[ 2818-66-8 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol Reflux;	Synthesis of the Probe 1 The probe 1 was prepared by condensation of 5-amino-2- mercaptobenzimidazole with 3-formylchromone in a 1:1 stoichiometry in methanolic solution under reflux condition. A bright yellow solid product was obtained, filtered and dried in vacuo. The synthesized ligand was spectroscopically characterized by employing UV-vis, FT-IR,Mass and 1H and 13C NMR studies. [C17H13N3O2S], 1: Yield: 80%, M.P: 185 °C, FTIR: 1604 ν(HC=N), 1641 ν(C=O), 1442 ν(C - N), 847 ν(C - S). UV - vis (λmax, nm): 237, 277 (π - π*). 1H NMR (ppm): 12.39 (-SH), 9.26 (HC=N), 7.9-6.9 (Ar - H). 13C NMR (ppm): 180.09 (C=O), 168.61 (C=N), 156.10 (C - N), 135.45-112.20 (Ar - C). ESI - MS (m/z) : 323 [C17H13N3O2S]+, 321 [C17H13N3O2S-2H]+.

References: [1]Zehra, Siffeen; Khan, Rais Ahmad; Alsalme, Ali; Tabassum, Sartaj [Journal of Fluorescence, 2019, vol. 29, # 4, p. 1029 - 1037].

46
[ 770-05-8 ]
[ 17422-74-1 ]
C₁₈H₁₅NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.6%	With triethylamine; In methanol;	In total, 1 mmol of <strong>[770-05-8]octopamine hydrochloride</strong>, 1 mmol triethylamine, and 1 mmol of chromone-3-carboxaldehyde were dissolved in 5 mL of MeOH. The reaction solution was stirred until white powder was formed, and the resulting powder was filtered and washed with acetone and ether. Yield: 116.3 mg (37.6%). 1H NMR (400 MHz in DMSO-d6, 20C): delta = 10.24 (s, 1H), delta = 9.30(s, 1H), delta = 7.77 (d, J = 8.1 Hz, 1H), delta = 7.44 (t,J = 8.2 Hz, 1H), delta = 7.31 (d, J = 12 Hz, 1H), delta = 7.18 (d,J = 8.2 Hz, 2H), delta = 7.05 (m, 2H), delta = 6.73 (d, J = 8 Hz,2H), delta = 5.63 (s, 1H), delta = 5.55 (t, J = 8 Hz, 1H), delta = 4.59(m, 1H), 3.46 (m, 1H). 13C NMR (700 MHz in DMSO-d6, 20 C, ppm): delta = 177.91, 156.51, 154.86, 133.18, 127.09,125.24, 123.16, 121.48, 117.52, 114.81, 101.52, 99.27,71.52, 56.22, 54.41. ESI-MS for C18H15NO4 + H+, Calcd,310.11 (m/z); found, 309.92. Elemental analysis Calcd (%)for C18H15NO4 + CH3OH: C, 66.85; H, 5.61; N, 4.10%;found (%): C, 66.69; H, 5.61; N, 3.99%.

References: [1]Bulletin of the Korean Chemical Society,2020,vol. 41,p. 201 - 204.

47
[ 5031-78-7 ]
[ 17422-74-1 ]
[ 2413150-75-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With silica supported perchloric acid In methanol at 20℃;	2.1.4. General Procedure for Synthesis of 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-One Derivatives (3a-u) & 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenylboronic Acid Derivatives(5a-h) General procedure: A mixture of 6/7/8-substituted-3-formyl-4H-chromen-4-one (1a-i, 1.414 moles) and substituted acetophenone/pacetylphenylboronicacid (2a-c/4, 0.9433 moles) was dissolvedin methanol (7.5 ml) and silica-supported perchloricacid (0.035 g, 0.22 mmol) was added to the above solutionand stirred at room temperature till the reactants were completelyconsumed (Scheme 1 & 2, monitored by TLC,EtOAc/CHCl3:C6H14, variable ratio). The methanol wasevaporated under reduced pressure and the resultant cruderesidue was extracted with dichloromethane. The organiclayer was separated and dried over sodium sulfate. The solvent was evaporated to get the crude mixture. Thereafter, theobtained products were purified through recrystallizationusing EtOAc as a solvent and the remaining were subjected toflash column chromatography (silica gel 60-120 mesh, eluentHexane::EtOAc) to yield the purified chromen-4-one-3-ylchalcones (3a-u & 5a-h) as solid powders. The structures ofthese newly obtained chromeno-chalcones (3a-u & 5a-h) werecharacterized spectroscopically (1H-NMR, 13C-NMR, UV, IRand Mass Spectroscopy) [22,23].

References: [1]Bhatia, Richa Kaur; Singh, Lakhwinder; Garg, Ruchika; Kaur, Maninder; Yadav, Manmohan; Madan, Jitender; Kancherla, Satyavathi; Pissurlenkar, Raghuvir R. S.; Coutinho, Evans C. [Medicinal Chemistry, 2020, vol. 16, # 2, p. 212 - 228].

48
[ 1129-65-3 ]
[ 17422-74-1 ]
[ 2409792-55-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With boron trichloride In dichloromethane at 20℃; regioselective reaction;
84%	With boron trichloride In dichloromethane at 20℃; for 5h;	3-(2-Aryl-3-fluoro-1H-inden-1-yl)-4H-chromen-4-ones 6aa-6ah;General Procedure General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah.

References: [1]Sultana, Sabera; Lee, Yong Rok [Advanced Synthesis and Catalysis, 2020, vol. 362, # 4, p. 927 - 941].
[2]Kumari, Anupama; Fernandes, Rodney A. [Synthesis, 2020, vol. 52, # 15, p. 2245 - 2258].

49
[ 18829-55-5 ]
[ 17422-74-1 ]
[ 2447593-38-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With boron trifluoride diethyl ether complex; scandium trifluoromethanesulphonate In toluene at 80℃; for 12h;
84%	With (S)-diphenylprolinol In ethanol at 60℃; Green chemistry;

References: [1]Sultana, Sabera; Rubio, Peter Yuosef M.; Khanal, Hari Datta; Lee, Yong Rok [Organic Letters, 2022, vol. 24, # 24, p. 4360 - 4364].
[2]Akhtar, Muhammad Saeed; Thombal, Raju S.; Inductivo Tamargo, Ramuel John; Yang, Won-Guen; Kim, Sung Hong; Lee, Yong Rok [Green Chemistry, 2020, vol. 22, # 14, p. 4523 - 4531].

50
[ 3913-81-3 ]
[ 17422-74-1 ]
[ 2447593-45-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With (S)-diphenylprolinol In ethanol at 60℃; Green chemistry;
81%	With boron trifluoride diethyl ether complex; scandium trifluoromethanesulphonate In toluene at 80℃; for 12h;

References: [1]Akhtar, Muhammad Saeed; Thombal, Raju S.; Inductivo Tamargo, Ramuel John; Yang, Won-Guen; Kim, Sung Hong; Lee, Yong Rok [Green Chemistry, 2020, vol. 22, # 14, p. 4523 - 4531].
[2]Sultana, Sabera; Rubio, Peter Yuosef M.; Khanal, Hari Datta; Lee, Yong Rok [Organic Letters, 2022, vol. 24, # 24, p. 4360 - 4364].

51
[ 13667-12-4 ]
[ 17422-74-1 ]
3-(2-(4-bromophenyl)-3-fluoro-1H-inden-1-yl)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 2h;	General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah.

References: [1]Synthesis,2020,vol. 52,p. 2245 - 2258.

52
[ 10075-85-1 ]
[ 17422-74-1 ]
[ 2647930-90-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With indium(III) triflate In chlorobenzene at 80℃; for 12h; regioselective reaction;

References: [1]Sultana, Sabera; González-Montiel, Gisela A.; Pradhan, Samjhana; Khanal, Hari Datta; Nale, Sagar D.; Cheong, Paul Ha-Yeon; Lee, Yong Rok [ACS Catalysis, 2021, vol. 11, p. 6467 - 6473].

53
[ 769-26-6 ]
[ 17422-74-1 ]
C₂₀H₁₈O [ No CAS ]

References: [1]ACS Catalysis,2021,vol. 11,p. 6467 - 6473.

54
[ 326-91-0 ]
[ 17422-74-1 ]
[ 4860-93-9 ]
[ 2715076-44-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	In water at 60 - 70℃; for 1.5h; Green chemistry;	General procedure for the reaction of 4-oxo-4H-chromene-3-carboxaldehyde, 2-thenoyl-trifluoroacetone, and cyclic active methylene compounds: Synthesis of thetarget products 4a-c and 6a-c General procedure: A mixture of 4-oxo-4H-chromene-3-carboxaldehyde (1) (0.35 g, 2 mmol), 2-thenoyl-trifluoroacetone(2) (0.44 g, 2 mmol), and cyclic active methylene compounds 3a-c and5a-c (2 mmol) in distilled H2O (40 mL) was stirred and heated at 60-70 C for theappropriate time (75-120 min). The completion of the reaction was confirmed by TLC(EtOAc-petroleum ether 2:1) every 15 min. The resulting precipitate was separated byfiltration and washed with water then crystallized from diluted EtOH. 4-(4-Oxo-4H-chromen-3-yl)-3-phenyl-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-1,4-dihydropyrano[2,3-c]pyrazole (4a)Yellow solid; yield 88%; mp 203-205 C. IR (KBr), (v max, cm1): 3205 (br, NH), 1685(COketone), 1637 (COpyrone), 1616 (CC). 1H-NMR (400 MHz, DMSO-d6): 5.30 (s,1H, H-4), 6.92-6.97 (m, 1H, H-4thienyl), 7.14-7.21 (m, 2H, H-6chromone and H-3thienyl),7.33-7.46 (m, 4H, Ph-H, H-8chromone and H-5thienyl), 7.59 (d, 2H, J8.4 Hz, Ph-H),7.66-7.78 (m, 2H, H-7chromone and Ph-H), 8.01 (d, 1H, J8.4 Hz, H-5chromone), 8.80 (s,1H, H-2chromone), 11.17 (s, 1H, NH). 13C-NMR (100 MHz, DMSO-d6): 22.7 (C-4), 107.8(C-5), 110.9 (C-3a), 115.1 (q, J235.1 Hz, CF3), 118.8 (C-3chromone), 119.6 (C-8chromone),123.8 (C-4achromone), 124.5 (C-5chromone), 125.5 (C-6chromone), 128.2 (C-2,6phenyl), 128.7 (C-4phenyl), 129.0 (C-3,5phenyl), 130.9 (C-4thienyl), 132.2 (C-1phenyl), 133.7 (C-5thienyl),134.4 (C-3thienyl), 134.6 (C-7chromone), 143.7 (C-3), 145.3 (C-2thienyl), 150.7 (C-2chromone),155.6 (C-8achromone), 156.2 (C-6), 159.3 (C-7a), 164.6 (COketone), 175.9 (COpyrone).MS (m/z, I %): 520 (M, 5%). Anal. Calcd for C27H15F3N2O4S (520.49): C, 62.31%; H,2.90%; N, 5.38%; S, 6.16%. Found: C, 62.12%; H, 2.74%; N, 5.19%; S, 5.97%

References: [1]Ali, Tarik E.; Assiri, Mohammed A.; Alzahrani, Abdullah Y.; Salem, Mohamed A.; Shati, Ali A.; Alfaifi, Mohammad Y.; Elbehairi, Serag Eldin I. [Synthetic Communications, 2021, vol. 51, # 21, p. 3267 - 3276].

55
[ 17422-74-1 ]
[ 109-77-3 ]
[ 4860-93-9 ]
[ 2509414-65-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	In water monomer at 80℃; for 1h;	General procedure for the synthesis of compounds4a-4d and 6a-6d. General procedure: A mixture of 4-oxo-4Hchromene-3-carbaldehyde (1, 2.5 mmol), malononitrile(2, 2.5 mmol), and cyclic active methylene compound 3a-3d or 5a-5d (2.5 mmol) in distilled water (50 mL)was stirred at 80°C for 60-90 min. The progress of thereaction was monitored by TLC (ethyl acetate-petroleumether, 2:1) every 15 min. After completion of thereaction, the precipitate was separated by filtration andrecrystallized from ethanol.

References: [1]Ali; Assiri; Shati; Alfaifi; Elbehairi [Russian Journal of Organic Chemistry, 2022, vol. 58, # 1, p. 106 - 113][Zh. Org. Khim., 2022, vol. 58, # 1, p. 106 - 113].

56
[ 17422-74-1 ]
[ 109-77-3 ]
[ 41927-50-8 ]
[ 2763390-17-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	In water monomer at 80℃; for 1h;	General procedure for the synthesis of compounds4a-4d and 6a-6d. General procedure: A mixture of 4-oxo-4Hchromene-3-carbaldehyde (1, 2.5 mmol), malononitrile(2, 2.5 mmol), and cyclic active methylene compound 3a-3d or 5a-5d (2.5 mmol) in distilled water (50 mL)was stirred at 80°C for 60-90 min. The progress of thereaction was monitored by TLC (ethyl acetate-petroleumether, 2:1) every 15 min. After completion of thereaction, the precipitate was separated by filtration andrecrystallized from ethanol.

References: [1]Ali; Assiri; Shati; Alfaifi; Elbehairi [Russian Journal of Organic Chemistry, 2022, vol. 58, # 1, p. 106 - 113][Zh. Org. Khim., 2022, vol. 58, # 1, p. 106 - 113].

57
[ 6050-80-2 ]
[ 17422-74-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine In ethanol at 80℃; for 1.5h;

References: [1]Wang, Wei-Na; Liu, Ren-Ming; Zhang, Lei; Liu, Xiong-Li; Dai, Yi-Feng; Yu, Zhang-Biao; Peng, Li-Jun [Organic and Biomolecular Chemistry, 2022, vol. 20, # 11, p. 2227 - 2232].

58
[ 4765-56-4 ]
[ 17422-74-1 ]
[ 2766838-90-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide at 150℃; for 0.833333h; Microwave irradiation;
	In N,N-dimethyl-formamide at 150℃; Microwave irradiation;

References: [1]Yun, Ei Seul; Akhtar, Muhammad Saeed; Mohandoss, Sonaimuthu; Lee, Yong Rok [Organic and Biomolecular Chemistry, 2022, vol. 20, # 16, p. 3397 - 3407].
[2]Lv, Xueyan; Lv, Lili; Li, Shichen; Ding, Chengcheng; Yang, Bingchuan; Ma, Chen [Molecules, 2023, vol. 28, # 21].

59
[ 17422-74-1 ]
[ 6097-26-3 ]
[ 2755933-51-6 ]
[ 2755933-44-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 50 % 2: 28 %	With triethylamine In acetonitrile at 20℃; Overall yield = 58 percent;	4.2. General procedure for the synthesis of the compound 3a and 3a inMeCN General procedure: 3-Formylchromone 1a (1mmol, 0.174 g), phenacyl thiocyanate 2a (1mmol, 0.177 g) andEt3N (1mmol, 0.101 g) were added in acetonitrile (2ml) and stirred at room temperature.The reaction progress was monitored by TLC (E:H/1:5). After completion, the precipitatewas filtered and the products 3a and 3a were purified on silica gel TLC plates (E:H/1:5).

References: [1]Alizadeh, Abdolali; Rezaiyehraad, Reza [Journal of Sulfur Chemistry, 2022, vol. 43, # 3, p. 264 - 274].

60
[ 19788-36-4 ]
[ 17422-74-1 ]
[ 3052306-13-2 ]

Yield	Reaction Conditions	Operation in experiment
13 %	With indium trifluoride In toluene Reflux;	3.3.6. General Procedure for the Synthesis of Conjugates 6a, 6b, and 6d General procedure: Conjugates 6a, 6b, and 6d were prepared by the general procedure adopted from theliterature report [50]. A mixture of 4-oxo-4H-1-benzopyran-3-yl-carboxaldehyde (2a, 0.5 g,2.9 mmol) or methoxy-substituted 4-oxo-4H-1-benzopyran-3-yl-carboxaldehyde (2b/2c/2d,0.58 g, 2.9 mmol), (3,5-Dimethyl-isoxazol-4-yl)-methanol (0.80 g, 6.3 mmol), InF3 (24 mg, 1.43mmol, 5 mol%) and Toluene (5 mL) was taken in a round bottom flask fitted with a refluxcondenser. The mixture was refluxed for 5 h (125 C). After completion of the reaction, thereaction mixture was filtered to remove the catalyst and washed with toluene. The solventwas then evaporated in a vacuum, and the resulting precipitate was purified via columnchromatography on basic alumina to afford 6a, 6b, and 6d as white solids. Conjugate 6c wasnot obtained during the reaction as Starting Material 2c was left unreacted. 3-(Bis((3,5-dimethylisoxazol-4-yl)methoxy)methyl)-4H-1-benzopyran-4-one (6a). Yield = 13%;Rf = 0.48 [ethyl acetate±petroleum ether 50:50]; IR (neat)max: 2925, 1650, 1611, 1574, 1465,1425, 1386, 1344, 1312, 1265, 1217, 1178, 1146, 1079, 1026, 883, 848, 818, 761, 741, 698, 674and 640 cm1; UV/vis (MeOH) : 303, 297, 227 nm; 1H NMR (400 MHz, CDCl3): 8.23(dd, J = 8.0, 1.5 Hz, 1H, H-5), 8.13 (s, 1H, H-2), 7.70 (ddd, J = 8.7, 7.1, 1.7 Hz, 1H, H-7),7.59-7.36 (m, 2H, H-6 and H-8), 5.83 (s, 1H, H-10), 4.43 (dd, J = 35.3, 11.9 Hz, 2H, H-60 0), 2.36(s, 6H, 2xCH3), 2.26 (s, 6H, 2xCH3); 13C NMR (101 MHz, CDCl3): 176.12 (C-4 C=O),167.58 (C-50 0), 159.86 (C-30 0), 156.40 (C-8a), 154.93 (C-2), 134.23 (C-7), 126.01 (C-6), 125.78(C-5), 124.23 (C-4a), 121.56 (C-3), 118.38 (C-8), 110.78 (C-40 0), 95.73 (C-1), 58.19 (C-60 0), 11.19(CH3), 10.28 (CH3); HRMS (ESI-TOF) (m/z) C22H22N2O6 calculated, 433.1376, found433.1302 [M + Na]+; and calculated, 449.1115, found, 449.1039 [M + K]+.

References: [1]Gupta, Shilpi; Park, Shang Eun; Mozaffari, Saghar; El-Aarag, Bishoy; Parang, Keykavous; Tiwari, Rakesh Kumar [Molecules, 2023, vol. 28, # 10].

61
[ 19788-36-4 ]
[ 17422-74-1 ]
[ 3052306-18-7 ]

Yield	Reaction Conditions	Operation in experiment
29 %	Stage #1: 3-Formylchromone With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 100℃; Stage #2: 4-hydroxymethyl-3,5-dimethylisoxazole In tetrachloromethane at 0 - 20℃;	3.3.8. Synthesis of Conjugate 8a Conjugate 8a was prepared via the general procedure adopted from the literature report[51]. Amixture of 4-oxo-4H-1-benzopyran-3-yl- carboxaldehyde (2a, 0.5 g, 2.9mmol), NBS(0.61 g, 3.44 mmol), and AIBN (20 mg) in CCl4 (25 mL) was taken in a round bottom flask andrefluxed for 1 h. The mixture was then cooled in an ice-water bath, followed by the addition of(3,5-dimethyl-isoxazol-4-yl)-methanol (0.73 g, 5.74 mmol). After stirring the reaction mixturefor 30 min at room temperature, the mixture was diluted with CH2Cl2 (100 mL), washed withwater, dried withMgSO4, and the solvent evaporated. The resulting precipitate was purifiedby column chromatography to afford 8a as white solid. For the Conjugates 8b, 8c, and 8d,StartingMaterials 2b, 2c, and 2d reacted and gave very complicated reactions, as indicated byTLC’s, and Products 8b, 8c, and 8d could not be isolated in pure form.(3,5-Dimethylisoxazol-4-yl)methyl 4-oxo-4H-1-benzopyran-3-carboxylate (8a). Yield = 29%;Rf = 0.5 [ethyl acetate±petroleum ether 50:50]; IR (neat)max: 3055, 2957, 2923, 2867, 2350,2082, 1705, 1655, 1614, 1569, 1508, 1463, 1426, 1383, 1339, 1311, 1291, 1263, 1201, 1151, 1115,1103, 1085, 1056, 1033, 971, 957, 938, 900, 873, 855, 813, 791, 771, 750, 739, 686, 675 and634 cm1; UV/vis (MeOH) : 293, 225 nm; 1H NMR (400 MHz, CDCl3): 8.62 (s, 1H, H-2),8.26 (dd, J = 8.0, 1.5 Hz, 1H, H-5), 7.70 (ddd, J = 8.7, 7.1, 1.7 Hz, 1H, H-7), 7.50-7.44 (m, 2H,H-6 and H-8), 5.13 (s, 2H, -OCH2), 2.48 (s, 3H, CH3), 2.37 (s, 3H, CH3); 13C NMR (101 MHz,CDCl3): 173.29 (C-4 C=O), 168.80 (C-10 C=O), 163.31 (C-30 0), 162.12 (C-2), 159.97 (C-50 0),155.69 (C-8a), 134.45 (C-7), 126.69, 126.52 (C-6 and C-5), 125.20 (C-4a), 118.30 (C-8), 115.97(C-3), 109.67 (C-40 0), 56.07 (C-60 0 OCH2), 11.34 (CH3), 10.26 (CH3); HRMS (ESI-TOF) (m/z)C16H13NO5 calculated, 300.0872, found 300.0825 [M + H]+; calculated, 322.0691, found,322.0640 [M + Na]+; and calculated, 338.0431, found, 338.0378 [M + K]+.

References: [1]Gupta, Shilpi; Park, Shang Eun; Mozaffari, Saghar; El-Aarag, Bishoy; Parang, Keykavous; Tiwari, Rakesh Kumar [Molecules, 2023, vol. 28, # 10].

62
[ 956386-24-6 ]
[ 17422-74-1 ]
[ 3009020-23-6 ]

Yield	Reaction Conditions	Operation in experiment
85 %	In methanol at 80℃; Inert atmosphere;	1.2 In a 50ml round-bottomed flask containing 20ml of organic solvent methanol, add 6-hydroxypyridine hydrazide (A) (0.153g, 1mmol) and chromone-3-carbaldehyde (B) (0.174g, 1mmol) respectively, stir and dissolve , in N2Under protection, the reaction system was heated to 80°C and stirred under reflux for 3 hours. TLC tracking reaction detection. After the reaction is completed, the reaction system is cooled to room temperature, the solvent is distilled off under reduced pressure, and the crude product is recrystallized (DMSO:H2O=1:20) was purified to obtain yellow solid fluorescent probe CPP (0.26g, 85%),

References: [1]Current Patent Assignee: JIANGSU UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN117003742, 2023, A Location in patent: Paragraph 0020; 0023; 0024.

63
[ 17422-74-1 ]
[ 105-36-2 ]
[ 1768-59-8 ]
[ 3104103-59-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium acetate In ethanol at 50℃; for 0.5h; Sonication;	General procedure for synthesis of the products 3a-g and 5. General procedure: A mixture of equimolar amounts of phenyl hydrazine (0.27 ml, 2.5 mmol) and alkyl(aryl) isothiocyanate (2.5 mmol) was stirred at room temperature in absolute ethanol(10 ml) under ultrasound irradiation for 10 min to give the corresponding thiosemicarbazide1a-g and 4. Then, a solution of 3-formylchromone (2) (0.43 g, 2.5 mmol) and ethyl bromoacetate (0.27 g, 2.5 mmol) in absolute ethanol (10 mL) and freshly anhydrous sodium acetate (0.2 g) was added and sonicated at 50 oC for 20-30 min. The formed solids after cooling were filtered off and washed three times with water. The obtained solids were crystallized from ethanol to afford the target compounds 3a-g and 5.

References: [1]Ali, Tarik E.; Assiri, Mohammed A.; Shati, Ali A.; Alfaifi, Mohammad Y.; Elbehairi, Serag E. [Journal of Sulfur Chemistry, 2025, vol. 46, # 6, p. 1055 - 1076].

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• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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CAS No.: 17422-74-1

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CAS No.: 17422-74-1

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Product Details of 3-Formylchromone

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[ 17422-74-1 ] Synthesis Path-Downstream 1~63

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