64915-37-3

Upstream product

• 108656-11-7 2-(2-formyl-5-methoxyphenoxy)acetonitrile 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 60795-12-2 2-hydroxy-4-methoxy-ω-nitroacetophenone 
• 13710-73-1 4-hydroxy-7-methoxy-3-nitro-chromen-2-one 
• 65795-30-4 7-methoxy-3-nitro-chromen-4-one 

Relevant academic research and scientific papers

NHC-catalyzed green synthesis of functionalized chromones: DFT mechanistic insights and: In vitro activities in cancer cells

An efficient synthesis of 3-aminochromones and 3-alkylchromones by a N-heterocyclic carbene (NHC) catalyzed intramolecular hydroacylation reaction of corresponding salicylaldehyde derived nitriles and activated alkynes respectively in ionic liquids under microwave conditions is reported. This protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, and convenient operation using the commercially available thiazolium catalyst. The origin of the chemical reactivity of the NHC-catalyzed intramolecular hydroacylation reaction of nitriles is studied using Density Functional Theory (DFT). The results suggest that 3-aminochromone formation occurs via an acyl anion intermediate called a Breslow intermediate (INT2) through TS2. The Breslow intermediate (INT2) forms a carbon-carbon bond with the nitrile carbon to produce an imine intermediate INT3viaTS3, which further undergoes imine to amine tautomerism to give the end product. Some of the derivatives of 3-aminochromone are subjected to amine functionalization in one pot to obtain a library of compounds for anticancer activity. Among the investigated compounds, 2c (SVM-2), 4c (SVM-4) and 2d (SVM-9) show IC50 values of 5.18, 4.89 and 27.3 μM respectively in HeLa S3 cancer cells. Compound 5c (SVM-5) shows IC50 values of 13.3 and 14.2 μM in A549 and HeLa S3 cancer cells, respectively. Compounds 2c (SVM-2) and 4c (SVM-4) produce morphological changes and control the colony formation in HeLa S3 cells, which indicates that these small molecules are potential candidates for anticancer drugs.

N-heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: An easy access to 3-aminochromones

(Figure presented) An immense effort has been made to develop an efficient strategy for the carbon-carbon bond formation between aldehyde and nitrile intramolecularly using an N-heterocyclic carbene catalyst to derive 3-aminochromone derivatives In good to excellent yields (80-95%).

Synthesis of 4,10-Dihydro-4,10-dioxo-1H--benzopyranopyridine, 4,5-Dihydro-4,5-dioxo-1H--benzopyranopyridine and 1,5-Dihydro-1,5-dioxo-4H--benzopyranopyridine derivatives from Aminobenzopyrones

3-Aminochromone and 3-aminocoumarin were condensed with diethyl ethoxymethylenemalonate and with dimethyl acetylenedicarboxylate to give intermediates, which were thermally cyclized to give 4,10-dihydro-4,10-dioxo-1H--benzopyranopyridinecarboxylates and 1,5-dihydro-1,5-dioxo-4H--benzopyranopyridinecarboxylates. 2-Aminochromone was converted to 4,5-dihydro-4,5-dioxo-1H--benzopyranopyridinecarboxylate via an intermediate condensation product with diethyl ethoxymethylenemalonate.These esters were hydrolyzed to the corresponding carboxylic acids (21, 30, 36, 50, and 60).Attempts to prepare 4,5-dihydro-4,5-dioxo-1H--benzopyranopyridinecarboxylates from 4-aminocoumarin were unsuccessful.

(4-Oxo-4H-1-benzopyran-3-yl)aminooxoacetic acids and their derivatives

The present invention relates to compounds of the formula: STR1 wherein R1 is hydrogen, halogen, hydroxy, lower alkoxy or lower alkyl, R2 is hydrogen or lower alkyl; R3 is hydrogen or lower alkyl. These compounds, includin

4,10-Dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-3-carboxylic acids, salts and esters

The present invention relates to 4,10-dihydro-4,10-dioxo-1H-1-benzopyrano[3,2-b]pyridine-3-carboxylic acids, salts and esters having the formula: STR1 wherein R1 is hydrogen, lower alkyl, halogen, hydroxy or lower alkoxy; R2 is hydrogen, aralkyl or lower alkyl; R3 is hydrogen or lower alkyl and their pharmaceutically acceptable salts. These compounds are indicated in the management of allergic conditions such as bronchial asthma, hay fever and the like.