Oxidative nucleophilic substitution of hydrogen versus ring-opening in the reaction of 4-r-2-nitrothiophenes with amines. The crucial effect of 4-alkyl groups

…, M Maccagno, G Petrillo, F Sancassan…

Index: Bianchi, Lara; Maccagno, Massimo; Petrillo, Giovanni; Sancassan, Fernando; Tavani, Cinzia; Morganti, Stefano; Rizzato, Egon; Spinelli, Domenico Journal of Organic Chemistry, 2007 , vol. 72, # 15 p. 5771 - 5777

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Citation Number: 21

Abstract

4-Alkyl-2-nitrothiophenes [10: R= CH3, CH (OH) CH3, CH (OCH3) CH3] react with secondary aliphatic amines, in the presence of AgNO3, to give 3-alkyl-2-amino-5- nitrothiophenes (12) through an oxidative nucleophilic substitution of hydrogen (ONSH) of synthetic interest. This behavior is in striking contrast with that of the parent 2-nitrothiophene (6), which was found to undergo ring-opening in analogous reaction conditions. A ...