Divergent reactivity in tandem reduction–Michael ring closures of five??and six??membered cyclic enones

…, B Nammalwar, LGM Slaughter

Index: Bunce, Richard A.; Nammalwar, Baskar; Slaughter, LeGrande M. Journal of Heterocyclic Chemistry, 2009 , vol. 46, # 5 p. 854 - 860

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Citation Number: 10

Abstract

The reductive cyclization of 2-nitrobenzyl ketones under dissolving metal conditions is well established as a route to the synthesis of indoles [1, 2]. Earlier work from our laboratory studied a tandem reduction–Michael addition variant of this reaction as a route to the synthesis of 1, 2, 3, 4-tetrahydroquinoline-2-acetic esters [3], and we have recently used this reaction to synthesize 1, 2, 3, 9-tetrahydro-4H-carbazol-4-one [4]. In this investigation, we ...