Sequential Addition/Elimination/Annulation Reactions of 4-Pentynones with Benzylamine and Ammonia

Antonio Arcadi; Elisabetta Rossi

doi:10.1055/s-1997-3242

Synlett 1997; 1997(6): 667-668
DOI: 10.1055/s-1997-3242

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Sequential Addition/Elimination/Annulation Reactions of 4-Pentynones with Benzylamine and Ammonia

Antonio Arcadi¹ , Elisabetta Rossi²

¹Dipartimento di Chimica Ingegneria Chimica e Materiali della Facoltà di Scienze, Università de L’Aquila, Via Vetoio, Coppito Due, I-67100 L’Aquila, Italy, Fax: 0039-862-433753; E-mail: arcadi@axscaq.aquila.infn.it
²Istituto di Chimica Organica della Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20139 Milano, Italy

Abstract

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The sequential addition/elimination/cycloammination of 4-pentynones in the presence of benzylamine or ammonia produces 1,2,3,-5-substituted and 2,3,5-substituted pyrroles and fused pyrrole systems, respectively in good to high yields. The methodology has been extended to the preparation of the 17β-hydroxyandrost-4-ene[3,2-b](1-benzyl-5-methyl)pyrrole.

4-pentynones - imines - annulation - pyrroles

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