Reductive smiles rearrangement of 1-[(5-chloro-2-nitrophenyl) sulfonyl]-1H-pyrrole-2-carbohydrazide to 1-amino-6-chloro-2-(1H-pyrrol-2-yl) benzimidazole

R Silvestri, A Pifferi, G De Martino, S Massa…

Index: Silvestri, Romano; Pifferi, Augusto; De Martino, Gabriella; Massa, Silvio; Saturnino, Carmela; Artico, Marino Heterocycles, 2000 , vol. 53, # 10 p. 2163 - 2174

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Citation Number: 14

Abstract

Abstract Treatment of 1-[(5-chloro-2-nitrophenyl) sulfonyl]-1H-pyrrole-2-carbohydrazide with powdered iron in glacial acetic acid afforded 1-amino-6-chloro-2-(1H-pyrrol-2-yl) benzimidazole as the sole product. This compound was also obtained by iron-acetic acid reduction of 1-(5-chloro-2-nitrophenyl)-1H-pyrrole-2-carbohydrazide. Splitting of the sulfone group occurred only in the presence of the carbohydrazide group. In fact, iron-acetic acid ...

~90%

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[Guillon, Jean; Grellier, Philippe; Labaied, Mehdi; Sonnet, Pascal; Leger, Jean-Michel; Deprez-Poulain, Rebecca; Forfar-Bares, Isabelle; Dallemagne, Patrick; Lemaitre, Nicolas; Pehourcq, Fabienne; Rochette, Jacques; Sergheraert, Christian; Jarry, Christian Journal of Medicinal Chemistry, 2004 , vol. 47, # 8 p. 1997 - 2009]