Synthesis Studies Of Chromenodihydropyridine Derivatives

Significant pharmacological action is demonstrated when chromoene and heterococycles containing nitrogen are combined.It is not only common in many different plants and natural medicines,but also serves as the structural backbone of many significant medications.It also has significant uses in the sectors of agriculture,food chemistry,and materials.As a result,the process for creating novel chromoene and nitrogen heterocycle frameworks has gained significance in the area of developing new drugs.The amphiphilic nuclear site greatly enhances the participation of 2-amino-4H-chromen-4-ones in the cycloaddition reaction to build a nitrogen-containing heterocycle and provides a broad synthetic potential for 2-amino-4H-chromen-4-ones.The presence of an amino group on 2-amino-4H-chromen-4-ones critically alters the reaction capacity of the pyranone ring relative to the nucleophile.As a result,the effective synthetic block 2-amino-4H-chromen-4-ones with dual parental nuclear sites was chosen,and three compounds with various nitrogen heterocyclic units were designed and created.The first part:ZnCl2 chloride promotes the cycloaddition of substitution of 2-amino-4H-chromen-4-ones,aryl aldehyde and 4,4-dimethoxycyclohexa-2,5-dien-1-one to obtain 4-hydroxy-1-methoxy-5-phenyl-5,6-dihydro-12H-chromeno[2,3-c]isoquinolin-12-one derivatives.Under optimal conditions,24 compounds were synthesized,and all products were characterized by infrared spectroscopy,high resolution mass spectroscopy,NMR spectroscopy,and single crystals were cultured to verify the stereostructure of three of the compounds.The second part:ZnCl2 promotes the three-component substitution of 2-amino-4H-chromen-4-ones,substituted aryl aldehyde and cyclohexane-1,3-dione in a one-pot way to obtain 11-phenyl-7,8,9,11-tetrahydro-10H-chromeno[2,3-b]quinoline-10,12(6H)-dione derivatives.Under optimal conditions,20 compounds were synthesized,all products were characterized by IR,high resolution mass spectroscopy,NMR spectroscopy,and single crystals were cultured to verify the stereostructure of two of the compounds.The third part:Cs2CO3 promotes the[3+3]cycloaddition of the substitution of 2-amino-4H-chromen-4-ones,(Z)-4-benzylidene-2-phenyloxazol-5(4H)-one derivatives to obtain the N-(2,5-dioxo-4-phenyl-1,3,4,5-tetrahydro-2H-chromeno[2,3-b]pyridin-3-yl)benzamide derivatives.Under optimal conditions,23 compounds were synthesized,and all the products were characterized by IR,high-resolution mass spectroscopy,and NMR spectroscopy.