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Paper | Regular issue | Vol 53, No. 4, 2000, pp.851-859
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8825
Dioximes as Synthons for Medium Ring Heterocyclic Compounds

Maya Shankar Singh* and Ashwani Kumar Singh

*Department of Chemistry, D. D. U. Gorakhpur University, Gorakhpur-273 009 (U. P.), India

Abstract

A simple and convenient synthetic approach to eight-, nine- and ten-membered nitrogen and oxygen containing heterocycles has been developed. 3,4-Diaryl-1,6,2,5-dioxadiazocines, (3) and (4), 3,4-diaryl-1,6,2,5-dioxadiazonines,(5) and 3,4-diaryl-1,6,2,5-dioxadiazacyclodeca-2,4-dienes (6) are prepared in one-pot from vicinal dioximes (1) via dianion intermediate (2) and 1,2-dibromoethylene, l,2-dichloroethane, 1,3-dibromopropane and 1,4-dichlorobutane, respectively. A plausible mechanism has bcen discussed.