The [1+ 4] cycloaddition of isocyanides with 1-aryl-2-nitro-1-propenes. Methyl 2-nitro-3-arylpropenoates and methyl 2-nitro-2, 4-pentadienoates. Synthesis of 1- …

A Foucaud, C Razorilalana-Rabearivony…

Index: Foucaud, Andre; Razorilalana-Rabearivony, Claudia; Loukakou, Emile; Person, Herve Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3639 - 3644

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Citation Number: 27

Abstract

The [1+ 41 cycloadditions of isocyanides with various aryl nitroalkenes have been investigated. When the aryl groups were XCsH4, naphthyl, and 2-pyridinyl, the reactions gave the 1-hydroxyindoles, 1-hydroxybenzoindoles, and 1-hydroxy-7-azaindole. When the aryl group was thienyl or furyl, fused 1-hydroxypyrroles were obtained. The reaction of isocyanide with methyl 2-nitro-2, 4-pentadienoates gave 1-hydroxypyrroles. A mechanism ...