Functional rearrangement of 3-Cl or 3,3-diCl-γ-lactams bearing a secondary 1-chloroalkyl substituent at C-4 |
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Authors: | Mariella Pattarozzi Fabrizio Roncaglia Andrew F Parsons |
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Institution: | a Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Organic Chemistry, Via Campi 183, I-41100 Modena, Italy b Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK |
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Abstract: | The study of the reaction with MeONa/MeOH of chlorinated γ-lactams, prepared from the atom transfer radical cyclization of N-allyl-α-perchloroamides, has been extended to the case of substrates carrying an exo halogen atom on a branched carbon. Only with secondary exo C-Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, which with trichloro-lactams can proceed further to give 4-alkylidene derivatives. From a practical point of view, the outcome of the reaction with di- or trichloro N-cinnamylamides is synthetically valuable, affording the 5-methoxy-1H-pyrrol-2(5H)-one or 3-benzylidenepyrrolidine-2,5-dione, respectively, in good to excellent yield. |
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Keywords: | Halocompound Radical reactions γ-Lactams Eliminations Rearrangements |
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