Synthesis 2012; 44(22): 3523-3533
DOI: 10.1055/s-0032-1317352
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Nitrogen-Containing Heterocycles via Ring-Closing Ene-Ene and Ene-Yne Metathesis Reactions: An Easy Access to 1- and 2-Benzazepine Scaffolds and Five- and Six-Membered Lactams

Erica Benedetti*
a  Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, via Valleggio 11, 22100, Como, Italy   Fax: +39(031)2386449   Email: andrea.penoni@uninsubria.it
b  Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) – FR 2769 UPMC Université Paris 06, C. 229, 4 Place Jussieu, 75005 Paris, France
,
Michela Lomazzi
a  Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, via Valleggio 11, 22100, Como, Italy   Fax: +39(031)2386449   Email: andrea.penoni@uninsubria.it
,
Francesco Tibiletti
a  Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, via Valleggio 11, 22100, Como, Italy   Fax: +39(031)2386449   Email: andrea.penoni@uninsubria.it
,
Jean-Philippe Goddard
b  Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) – FR 2769 UPMC Université Paris 06, C. 229, 4 Place Jussieu, 75005 Paris, France
,
Louis Fensterbank
b  Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) – FR 2769 UPMC Université Paris 06, C. 229, 4 Place Jussieu, 75005 Paris, France
,
Max Malacria
b  Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) – FR 2769 UPMC Université Paris 06, C. 229, 4 Place Jussieu, 75005 Paris, France
,
Giovanni Palmisano
a  Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, via Valleggio 11, 22100, Como, Italy   Fax: +39(031)2386449   Email: andrea.penoni@uninsubria.it
,
Andrea Penoni*
a  Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, via Valleggio 11, 22100, Como, Italy   Fax: +39(031)2386449   Email: andrea.penoni@uninsubria.it
› Author Affiliations
Further Information

Publication History

Received: 23 July 2012

Accepted after revision: 14 September 2012

Publication Date:
09 October 2012 (online)


Abstract

Novel regioselective ring closing ene-yne metathesis provided an efficient access to different substituted 1-benzazepine scaffolds. The reported synthetic approach could also be used as a powerful tool for the selective formation of a highly functionalizable 2-benzazepine core. This synthetic protocol was even proved to be an efficient way to obtain a functionalizable benzazocine ­derivative. By modifying the structure of the starting materials, the optimized cyclization finally proved to be a suitable technique to obtain five- and six-membered lactams, enhancing the synthetic application of our method. Five- and six-membered lactams were efficiently prepared by ring-closing metathesis involving the loss of ethylene moiety and affording highly functionalizable compounds showing both electron-withdrawing substituents and electron-donor groups.

Supporting Information

 
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