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Paper | Regular issue | Vol 78, No. 3, 2009, pp.691-698
Published online, 17th November, 2008
DOI: 10.3987/COM-08-11558
Synthesis of Nitrogen-Containing Heterocycles 12. Reactions of 2-Amino-1-benzylideneamino-1H-imidazoles with Dimethyl Acetylenedicarboxylate

Yoshiko Miyamoto*

*Department of Chemistry, School of Science, Kitasato University, 1-15-1, Kitasato, Sagamihara, Kanagawa 228-8555, Japan

Abstract

2-Amino-4-aryl-1-benzylideneamino-1H-imidazoles (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in benzene to give dimethyl 2-amino-1-benzylidene-amino-1H-pyrrole-3,4-dicarboxylates (3), benzonitriles (4) and dimethyl 1-(2-amino-1-benzylideneamino-4-aryl-1H-imidazole-5- yl)fumarates (5) in moderate to high yields. Compounds 3 and 4 were considered as the reaction products of the intermediary Diels-Alder adducts, dimethyl 1-amino-3-aryl-7-benzylideneamino-2,7-diazabicylo[2.2.1]hepta-2,5-diene-5,6-di-carboxylates (2), which were not isolated and decomposed in a retro Diels-Alder reaction. The products 5 resulted from a Michael conjugate addition reaction of 1 to DMAD.