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

André Augusto Gomes Faraco Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Avenida Antônio Carlos 6627, Belo Horizonte, Brazil

Maria Auxiliadôra F. Prado Departamento do Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Avenida Olegário Maciel 2360, Belo Horizonte, BrazilCorrespondence[email protected]

Ricardo J. Alves Departamento do Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Avenida Olegário Maciel 2360, Belo Horizonte, Brazil

José D. Souza Filho Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Avenida Antônio Carlos 6627, Belo Horizonte, Brazil

Rosemeire Brondi Alves Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Avenida Antônio Carlos 6627, Belo Horizonte, Brazil

Renata F. Prado Faraco Departamento do Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Avenida Olegário Maciel 2360, Belo Horizonte, Brazil

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

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

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