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Communication | Regular issue | Vol 9, No. 11, 1978, pp.1561-1570
Published online, 1st January, 1970
DOI: 10.3987/R-1978-11-1561
Simple Entry into the 1,6-Diazaphenalene Ring System

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

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


A facile synthesis of the dihydro-1,6-diazaphenalene ring system has been developed by heating one equivalent of methyl-1,2,3,4-tetrahydro-5-oxocoumarin-4-y1 acetate (5) with three equivalents of hydroxylamine hydrochloride in aqueous ethanol; 7,8-dihydro-2,5- dihydroxy-1,6-diazaphenalene-1,6-dioxide (2) was produced in this manner in 88% yield.