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Synfacts 2007(5): 0469-0469  
DOI: 10.1055/s-2007-968474
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Large Heterocyclic-Ring Fused Naphthoquinones

Contributor(s): Victor Snieckus, Todd Macklin
S. Yerushalmi, N. G. Lemcoff, S. Bittner*
Ben Gurion University of the Negev, Beer Sheva, Israel
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

Reported is the straightforward four-step synthesis of four unsymmetrical naphthoquinone-fused 8- (diazacine), 9- (diazecine), and 10- (diazonine) membered ring heterocycles in good overall yields. The method takes advantage of double Michael addition-elimination as a prelude to an RCM process affording the indicated heterocycles in modest to good overall yields. Detailed NMR analysis and experimental procedures are provided.