Synthesis of Eight-, Nine-, and Ten-Membered, Nitrogen-Containing Quinone-Fused Heterocycles

Abstract

A series of allylamino-, diallylamino-, homoallylamino- and bishomoallylamino naphthoquinones were synthesized. Ruthenium-mediated ring-closing metathesis (RCM) efficiently converted these substrates into novel eight-, nine-, and ten-membered quinone-fused heterocycles. Hydro-derivatives of diazacine, diazonine, and diazecine were isolated and characterized.

Key words

naphthoquinone - ring-closing metathesis - cyclization - heterocycles - diazacines - diazecines - diazonines

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