Issue 22, 2011
From the journal:

Organic & Biomolecular Chemistry

Silver-catalysed intramolecular cyclisation of 2-alkynylacetophenones and 3-acetyl-2-alkynylpyridines in the presence of ammonia

Monica Dell'Acqua,a   Giorgio Abbiati,*a   Antonio Arcadib  and  Elisabetta Rossia  

* Corresponding authors

a DISMAB – Sezione di Chimica Organica “A. Marchesini”, Università degli Studi di Milano, via G. Venezian, 21, Milano, Italia

b Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università degli Studi dell'Aquila, Via Vetoio, Coppito, L'Aquila, Italia
E-mail: giorgio.abbiati@unimi.it

Abstract

Silver-catalysed/microwave-assisted domino reactions of 2-alkynyl-acetophenones and 3-acetyl-2-alkynylpyridines in the presence of ammonia are widely described. In most cases the reaction give a mixture of the imino- and carbo-cyclisation products, with a general preference for the former. A plausible mechanism is proposed and the dual activity of silver salts is supported by NMR experiments.

Graphical abstract: Silver-catalysed intramolecular cyclisation of 2-alkynylacetophenones and 3-acetyl-2-alkynylpyridines in the presence of ammonia

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Article information

DOI
https://doi.org/10.1039/C1OB06271A
Article type
Paper
Submitted
27 Jul 2011
Accepted
16 Aug 2011
First published
16 Aug 2011

Org. Biomol. Chem., 2011,9, 7836-7848

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Silver-catalysed intramolecular cyclisation of 2-alkynylacetophenones and 3-acetyl-2-alkynylpyridines in the presence of ammonia

M. Dell'Acqua, G. Abbiati, A. Arcadi and E. Rossi, Org. Biomol. Chem., 2011, 9, 7836 DOI: 10.1039/C1OB06271A

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