Indole syntheses utilizing o-methylphenyl isocyanides.

Y Ito, K Kobayashi, N Seko, T Saegusa

Index: Ito; Kobayashi; Seko; Saegusa Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 1 p. 73 - 84

Full Text: HTML

Citation Number: 61

Abstract

New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2, 4-xylyl, and 2, 6-xylyl isocyanide is described in full detail. Treatment of o-tolyl isocyanide with LDA in diglyme at− 78° C generated selectively o-(lithiomethyl) phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similary, 2, 4-xylyl and 2, 6-xylyl isocyanides were cyclized to 5- ...

Related Articles:

Tandem copper-catalysed aryl and alkenyl amination reactions: the synthesis of N-functionalised indoles

[Hodgkinson, Roy C.; Schulz, Jurgen; Willis, Michael C. Organic and Biomolecular Chemistry, 2009 , vol. 7, # 3 p. 432 - 434]

Tandem copper-catalysed aryl and alkenyl amination reactions: the synthesis of N-functionalised indoles

[Hodgkinson, Roy C.; Schulz, Jurgen; Willis, Michael C. Organic and Biomolecular Chemistry, 2009 , vol. 7, # 3 p. 432 - 434]

Palladium??Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N??Acyloxazolinones as Ester Enolate Equivalents

[Trost, Barry M.; Michaelis, David J.; Charpentier, Julie; Xu, Jiayi Angewandte Chemie - International Edition, 2012 , vol. 51, # 1 p. 204 - 208]

More Articles...