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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 3
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Original Articles

Synthesis of Benzomacrolactam by 12-endo Selective Aryl Radical Cyclization of N-(4-Allyloxybutyl)-2-iodobenzamide

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Pages 463-474 | Received 22 Feb 2002, Published online: 17 Aug 2006
 

Abstract

Regioselective 12-endo aryl radical cyclization of N-(4-allyloxybutyl)-2-iodobenzamide (7) with tri-n-butyltin hydride provided benzomacrolactam 15. The structure of 15 is supported by 1H and 13C NMR spectroscopy and by DEPT, COSY, COSYLR and HMQC experiments.

Acknowledgments

A. G. Faraco, R. F. P. Faraco, M. A. F. Prado, and R. B. Alves thank Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for fellowships. The authors thank Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) for financial support.

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