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Synlett 2014; 25(07): 969-974
DOI: 10.1055/s-0033-1340960
DOI: 10.1055/s-0033-1340960
letter
Cyclization of Nitroacetamide Derivatives with a Tethered Phenyl Ring in Triflic Acid
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
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett. Included are full experimental details, representative 1H and 13C NMR spectra and X-ray data.
- Supporting Information
-
References and Notes
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