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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, Michela Lomazzi, Francesco Tibiletti, Jean-Philippe Goddard, Louis Fensterbank, Max Malacria, Giovanni Palmisano, Andrea Penoni*

*Dipartimento di Scienza e Alta Tecnologia, UniversitÓ degli Studi dell’Insubria, via Valleggio 11, 22100, Como, Italy, Email: andrea.penoniuninsubria.it

E. Benedetti, M. Lomazzi, F. Tibiletti, J.-P. Goddard, L. Fensterbank, M. Malacria, G. Palmisano, A. Penoni, Synthesis, 2012, 44, 3523-3533.

DOI: 10.1055/s-0032-1317352 (free Supporting Information)


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Abstract

Regioselective ring closing ene-yne metathesis provided an efficient access to different substituted 1-benzazepine scaffolds. Five- and six-membered lactams were efficiently prepared by ring-closing metathesis affording highly functionalizable compounds.

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Key Words

ring closing ene-yne metathesis, ring closing ene-ene metathesis, Grubbs catalysts, nitrogen heterocycles, regioselective reactions, benzazepine scaffolds, 3-pyrrolin-2-ones


ID: J66-Y2012-3680