Issue 12, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of benzolactams by 11-endo selective aryl radical cyclisation of 2-iodobenzamides

Maria A. F. Prado,†*a   Ricardo J. Alves,a   José D. Souza Filho,b   Rosemeire B. Alves,b   Maria T. C. Pedrosa,a   Renata F. Pradoa  and  André A. G. Faracob  

* Corresponding authors

a Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Avenida Olegário Maciel 2360, Belo Horizonte, Brazil

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

Abstract

Regioselective 11-endo aryl radical cyclisation of methyl 4-O-allyl-2,3-di-O-benzyl-6-deoxy-6-(2-iodobenzoylamino)-α-D-glucopyranoside 4 and N-(3-allyloxypropyl)-2-iodobenzamide 9 with tri-n-butyltin hydride provided the benzolactams 5 and 10, respectively. The unequivocal structures of 5 and 10 were supported by 1H and 13C NMR spectroscopy and by PENDANT or DEPT, COSY and HMQC experiments.

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Article information

DOI
https://doi.org/10.1039/B002416N
Article type
Paper
Submitted
27 Mar 2000
Accepted
20 Apr 2000
First published
31 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1853-1857

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Synthesis of benzolactams by 11-endo selective aryl radical cyclisation of 2-iodobenzamides

M. A. F. Prado, R. J. Alves, J. D. Souza Filho, R. B. Alves, M. T. C. Pedrosa, R. F. Prado and A. A. G. Faraco, J. Chem. Soc., Perkin Trans. 1, 2000, 1853 DOI: 10.1039/B002416N

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