Tetrahedron

Synthesis and reactions of 2-bis (methylthio) methylene-1-methyl-3-oxoindole: A facile access to benzo-and heterocyclo-fused carbazoles and indoles

MVB Rao, UKS Kumar, H Ila, H Junjappa

Index: Basaveswara Rao; Syam Kumar; Ila; Junjappa Tetrahedron, 1999 , vol. 55, # 38 p. 11563 - 11578

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Citation Number: 37

Abstract

The synthesis and reactions of 2-bis (methylthio) methylene-1-methyl-3-oxoindole 5 as a novel 3-carbon 1, 3-bielectrophilic component are described. Thus cycloaromatization of 5 with allyl, methallyl and crotyl Grignard reagents affords substituted carbazoles 12a-c in good yields. Cycloaromatization of 5 with various anions derived from aryl/heteroaryl acetonitriles and antipyrine gives novel benzo [c]-(16), naphtho [1, 2-c]-(19), indolo [3, 2-a] ...