Synlett 2014; 25(07): 969-974
DOI: 10.1055/s-0033-1340960
letter
© Georg Thieme Verlag Stuttgart · New York

Cyclization of Nitroacetamide Derivatives with a Tethered Phenyl Ring in Triflic Acid

Bamba Fanté*
a   Laboratoire de Chimie Organique Structurale, Université Félix Houphouët-Boigny, 22 BP 582 Abidjan 22, Côte d’Ivoire   Email: fante_bamba1@yahoo.fr
,
Yaya Soro
b   Laboratoire des Procédés Industriels de Synthèse, de l’Environnement et des Énergies Nouvelles, Institut National Polytechnique Félix Houphouët-Boigny, BP 991 Yamoussoukro, Côte d’Ivoire
,
Sorho Siaka
b   Laboratoire des Procédés Industriels de Synthèse, de l’Environnement et des Énergies Nouvelles, Institut National Polytechnique Félix Houphouët-Boigny, BP 991 Yamoussoukro, Côte d’Ivoire
,
Jérôme Marrot
c   Laboratoire ILV-UVSQ – UMR 8180 CNRS, 45 Avenue des États Unis, 78035 Versailles Cedex, France
,
Jean-Marie Coustard †
d   Laboratoire IC2MP-UMR 7285 CNRS, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
› Author Affiliations
Further Information

Publication History

Received: 03 December 2013

Accepted after revision: 19 February 2014

Publication Date:
24 March 2014 (online)


This publication is dedicated to the memory of Professor Jean-Marie Coustard who supervised this work but passed away at the end of August 2013. Rest in peace dear Professor.

Abstract

N-(3-Hydroxypropyl)-2-nitro-N-(ω-phenylalkyl)acetami-des underwent intramolecular cyclization in triflic acid to afford the corresponding hydroxyimino six- to nine-membered benzofused lactams. The six-membered derivative slowly transformed into 2-(3-hydroxypropyl)isoquinolin-3-one. NMR spectroscopic analysis in situ provided information on the cationic species involved in the reaction, permitting a mechanism to be postulated. This reaction provides a novel and simple route to benzofused lactams.

Supporting Information

 
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