1, 3-Dipolar Cycloaddition Reaction of 1-Methylperimidine 3-Ylides with Dimethyl Acetylenedicarboxylate

Abstract

3-Amino-1-methylperimidinium mesitylenesulfonate reacted with dimethyl acetylene-dicarboxylate (DMAD) in the presence of base to give dimethyl 1-(8-methylamino-1-naphthyl) pyrazole-3, 4-dicarboxylate, whereas the reaction of the 2-methyl congener gave dimethyl 7-methyl-7H-benzo [de] pyrazolo [3, 2-b] quinazoline-8, 9-dicarboxylate as a major product. The reaction of 1-methyl-3-phenacyl-and 3-methoxycarbonylmethyl-perimidinium bromides with DMAD gave dimethyl 1-(8-methylamino-1-naphthyl)-2-benzoyl-pyrrole-3, 4-dicarboxylate and trimethyl 1-(8-methylamino-1-naphthyl) pyrrole-2, 3, 4-tricarboxylate as major products, respectively.