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Communication | Regular issue | Vol 12, No. 7, 1979, pp.903-907
Published online, 1st January, 1970
DOI: 10.3987/R-1979-07-0903
Synthesis of 1,6-Diazaphenalene, a Vinylogous Imidazole

Jen-C. Chang, Mustafa I. El-Sheikh, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.

Abstract

The simple synthesis of a new heterocycle,1,6-diazaphenalene (2), a vinylogous imidazole is described; the key step in the synthesis was conversion of 7 to 8 by cleavage of the N-O bond followed by hydrogen shifts under modified Semmler Wolff conditions [CF3COOH, (CF3CO)2O, HCl].