Tetrahedron

Pyrolysis of quinoline-3, 4-dicarboxylic anhydrides bearing 2-phenyl, 2-benzyl and 2-o-tolyl substituents: formation of products of carbene insertion and addition

RFC Brown, KJ Coulston, FW Eastwood, MR Moffat

Index: Brown; Coulston; Eastwood; Moffat Tetrahedron, 1992 , vol. 48, # 36 p. 7763 - 7774

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Citation Number: 23

Abstract

Flash vacuum pyrolysis of 2-phenylquinoline-3, 4-dicarboxylic anhydride at 800°/0.06 mm gave indeno [1, 2-b] indole (30–40%), which readily added nucleophiles Y− at C-10 to give 5, 10-dihydro derivatives (Y H, Me, Ph, NEt2, OMe, CH (COOMe) 2 and CMe2NO2). Similar pyrolysis of the 2-benzylquinoline anhydride gave a 1: 2 mixture of the (expected) linear 5H-benzo [b] carbazole and the (unexpected) angular 7H-benzo [c] carbazole. The ...