Tetrahedron

Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl- …

P Haldar, G Barman, JK Ray

Index: Haldar, Pranab; Barman, Gopa; Ray, Jayanta K. Tetrahedron, 2007 , vol. 63, # 14 p. 3049 - 3056

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Citation Number: 21

Abstract

A simple methodology for the conversion of substituted N-aryl-γ-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-γ-lactam 2/3- carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4–I2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and ...