Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters |
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Authors: | Eliseu O. De Oliveira Carlos A. Brandt Richard A. Glennon |
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Affiliation: | a Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP 05508, Brazil b Department of Medicinal Chemistry, Virginia Commonwealth University, Richmond, VA 23298, USA c Instituto Butantan, São Paulo, SP 05503, Brazil |
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Abstract: | Novel 2-, and N-substituted 5-methylene-pyrrolidine benzamides and 2-, 3-, and N-substituted 5-methylene-2-pyrroline benzamides were synthesized for the first time in a straightforward manner and in good yields via iodocyclization of γ- and α-alkenyl-β-enaminoesters, respectively. The key step in the process is the synthesis of the methylene-pyrrolidine iodide and methylene-2-pyrroline iodide intermediates. Functional group inter-conversion of these iodides to their amino analogs, and their subsequent coupling to benzoic acids via EDC, afforded the above pyrrolidine/2-pyrroline-substituted benzamides in yields of around 75%. |
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Keywords: | Iodocyclization β-Enaminoesters Benzamides Pyrrolidines 2-Pyrrolines |
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