A Simple and Convenient Synthesis of Isolated-Fused Heterocycles Based on: 2-Imino- N -phenyl-2 H -chromene-3-carboxamide

Abstract

Starting from 2-imino-N-phenyl-2H-chromene-3-carboxamide, a series of functionalized chromene derivs. was prepd., such as, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one, and 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one. Furthermore, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one was elaborated into pyrazole derivs., tetrazole derivs., , 2-(2-benzylidenehydrazinyl)-3-phenyl-3H-chromeno[2,3-d]pyrimidin-4(10H)-one isoxazole, 5-chloro-1-(4-oxo-3-phenyl-4,10-dihydro-3H-chromeno[2,3-d]pyrimidin-2-yl)-3-phenyl-2,3-dihydro-1H-pyrazole-4-carbonitrile, pyrimidine derivs., pyridine derivs. benzo[b][1,4]oxazepin-2-amine, 3-chloro-4-(2-imino-2H-chromen-3-yl)-1-phenyl-4-(phenylamino)-2-azetidinone and 2-(2-imino-2H-chromen-3-yl)-3-phenyl-2-(Ph amino)thiazolidinone. The structures of these compds. were established by elemental anal., IR, MS and NMR spectral anal. The synthesis of the target compds. was achieved using 2-imino-N-phenyl-2H-1-benzopyran-3-carboxamide and (hydrazinyl)[1]benzopyrano[2,3-d]pyrimidinone in a reaction with 2,4-Pentanedione, 3-amino-2,4-dicyano-2-butenoic acid Et ester, propanedioic acid 1,3-di-Et ester, cyanoacetic acid Et ester, urea, 3-Oxobutanoic acid Et ester, (Ethoxymethylene)propanedinitrile, 3-amino-5-(methylthio)-1H-pyrazole-4-carbonitrile. [on SciFinder(R)]