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Report | Regular issue | Vol 20, No. 11, 1983, pp.2197-2202
Published online, 1st January, 1970
DOI: 10.3987/R-1983-11-2197
Reaction of 1-Methyl-Δ1(8)-dehydropyrrolizidine with Dimethyl Acetylenedicarboxylate

Seiji Miyano, Nobuko Mibu, Shinichiro Fujii, Osamu Yamashita, Hirokazu Annoura, and Kunihiro Sumoto

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


The reaction of 1-methyl-Δ1(8)-dehydropyrrolizidine with dimethyl acetylenedicarboxylate in hexane gave dimethyl 7-methyl-1,2,5,6-tetrahydro-3H-pyrrolo[1,2-a]azepine-8,9-dicarboxylate (3a) and dimethyl 1-methyl-1,2,5,6-tetrahydro-3H-pyrrolo[1,2-a]azepine-8,9-dicarboxylate (4a). The choice of protic solvent like methanol gave rise to the formation of a tricyclic compound.