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Paper | Regular issue | Vol 60, No. 1, 2003, pp.121-129
Published online, 25th November, 2002
DOI: 10.3987/COM-02-9630
Chlorination and Subsequent Cyclization to 1,3,4-Oxadiazoles of N1-Acyl-N3-cyanoguanidines and Related Compounds

Takayuki Suyama,* Tadashi Hasegawa, Motokazu Oda, Masahiko Tomaru, and Hiroyuki Ohkoshi

*Kanagawa Institute of Technology, Faculty of Engineering, Department of Applied Chemistry, Shimo-ogino, Atsugi-shi 243-02, Japan

Abstract

N1-Acyl-, N1-alkoxycarbonyl-, and N1-(N,N-dialkylcarbamoyl)guanidines bearing electron-withdrawing cyano or sulfonyl group at the N3-position were found to provide corresponding rearranged products, 1,3,4-oxadiazoles, when these guanidines were chlorinated by sodium hypochlorite followed by treating with base. Assignments of obtained compounds were accomplished by means of some reactions such as acid hydrolysis, alkoholysis, and catalytic hydrogenations, and of MS spectra.