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Report | Regular issue | Vol 22, No. 3, 1984, pp.549-559
Published online, 1st January, 1970
DOI: 10.3987/R-1984-03-0549
1-Azadienes as a Synthon for Heterocyclic Synthesis

Yoshiki Ohshiro,* Mitsuo Komatsu, Masatoshi Uesaka, and Toshio Agawa

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2-1 Yamadaoka, Toyonaka, Osaka 560-0043, Japan

Abstract

1-Azabutadienes 1 were found to be a good building block for three- to five-membered heterocycles having a functional group. Oxidation of 1 with mCPBA afforded 3-alkenyloxaziridines 2. Cycloaddition of 1 with ketenes gave the 4-alkenylazetidinones 6. Addition of a nitrile imine occurred across the C=N bond to give the 3-alkenyltriazoline 8, while that of a nitrile ylide occurred on the C=C bond to give the 3-formylpyrrole 14 formed by hydrolysis of the C=N bond.