Journal of the American Chemical Society

4+ 1 Radical annulations with isonitriles: a simple route to cyclopenta-fused quinolines

DP Curran, H Liu

Index: Curran, Dennis P.; Liu, Hui Journal of the American Chemical Society, 1991 , vol. 113, # 6 p. 2127 - 2132

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Citation Number: 140

Abstract

Abstract: Sunlamp irradiation of 1-substituted 5-iodo-l-pentynes, 5 equiv of phenyl isocyanide, and 1.5 equiv of hexamethylditin in tert-butylbenzene (0.01-0.025 M) at 150 OC produces 9-substituted 2, 3-dihydro-lH-cyclopenta [b] quinolines in 36-70% yields. A mechanistic proposal for this first example of a 4+ 1 radical annulation includes the following:(1) radical addition to an isonitrile,(2) cyclization of the resulting imidoyl radical ...

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