Reaction of phthalimidonitrene with furans

Abstract

2,5-Dimethylfuran reacts with phthalimidonitrene to give the 2-phthaloylhydrazone of cis-hex-3-ene-2,5-dione. Monosubstituted furans including the 2-methyl, 2-methoxy-, 2-phenyl, and 2-methoxycarbonyl derivatives react similarly, as do 1,3-diphenylbenzo[c] furan and 4,7-dihydro-1,3-diphenylbenzo[c]furan.The product of the last reaction is readily converted into 2-amino-1,3-diphenylisoindole. Reaction of phthalimidonitrene with 1,4-di-phenyl-2-benzopyran-3-one affords 2,3-diphenyl-1-phthalimidoindole through initial 1,2-addition.