Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

…, T Roca, M Monerris, D García-Díaz

Index: Bennasar, M. Lluisa; Roca, Tomas; Monerris, Manuel; Garcia-Diaz, Davinia Journal of Organic Chemistry, 2006 , vol. 71, # 18 p. 7028 - 7034

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Citation Number: 64

Abstract

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1, 4-dihydroquinolines, and 1, 2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis ( ...