Elsevier

Tetrahedron Letters

Volume 48, Issue 36, 3 September 2007, Pages 6393-6396
Tetrahedron Letters

Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters

https://doi.org/10.1016/j.tetlet.2007.06.166Get rights and content

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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Acknowledgment

The present work was supported in part by CAPES—Program PDEE-BEX0866/00-8, Brazil.

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