Tetrahedron

A convenient synthesis of 2-substituted indoles by the reaction of 2-(chloromethyl) phenyl isocyanides with organolithiums

K Kobayashi, D Iitsuka, S Fukamachi, H Konishi

Index: Kobayashi, Kazuhiro; Iitsuka, Daisuke; Fukamachi, Shuhei; Konishi, Hisatoshi Tetrahedron, 2009 ,  vol. 65,  # 36  p. 7523 - 7526

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Citation Number: 16

Abstract

The reaction of 2-(chloromethyl) phenyl isocyanides, readily available by dehydration of the respective N-[2-(chloromethyl) phenyl] formamides, with organolithiums produced 2- substituted indoles in satisfactory yields through addition of organolithiums to the isocyano carbon followed by intramolecular substitution reaction of the resulting imidoyl anion intermediates.