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Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide |
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| Authors: | Khaoula Jebali Aïcha Arfaoui Fatma Saâdi Jacques Lebreton |
| Institution: | 1. Laboratory of Selective Organic Synthesis and Biological Activity, Faculty of Science , El Manar University , Tunis , Tunisia;2. Laboratoire de Synthèse Organique, CNRS UMR, Faculté des Sciences et des Techniques , Nantes , France |
| Abstract: | We describe a simple and efficient protocol for accessing some unsaturated heterocyclic compounds in a direct evaluation of allyl bromide as Z-ethyl 3-bromomethyl-4-oxopent-2-enoate. The latter reacts with primary amines via two successive nucleophilic substitutions followed by a 5-exo-trig cyclization to produce selectively 4-acetyl-1-alkyl-1H-pyrrol-2(5H)-ones in good yields. |
| Keywords: | 5-Exo-trig cyclization primary amines pyrrol-2(5H)-ones Z-ethyl 3-bromomethyl-4-oxopent-2-enoate |