Synthesis 2013; 45(8): 1076-1082
DOI: 10.1055/s-0032-1318478
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine-Catalyzed Aza-Prins Cyclization: Metal-Free Synthesis and Antiproliferative Activity of Hexahydrobenzo[f]isoquinolines

Carlos A. M. Figueiredo
a   Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil   Fax: +55(128)155579   eMail: luizfsjr@iq.usp.br
,
K. R. Kishore K. Reddy
a   Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil   Fax: +55(128)155579   eMail: luizfsjr@iq.usp.br
,
Paula A. Monteiro
b   Divisão de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, 13083-970 Campinas, SP, Brazil
,
João E. de Carvalho
b   Divisão de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, 13083-970 Campinas, SP, Brazil
,
Ana L. T. G. Ruiz
b   Divisão de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, 13083-970 Campinas, SP, Brazil
,
Luiz F. Silva Jr*
a   Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil   Fax: +55(128)155579   eMail: luizfsjr@iq.usp.br
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Publikationsverlauf

Received: 30. Januar 2013

Accepted after revision: 25. Februar 2013

Publikationsdatum:
13. März 2013 (online)


Abstract

A series of hexahydrobenzo[f]isoquinolines were synthesized by an iodine-catalyzed aza-Prins cyclization under metal-free conditions. An aliphatic or an aromatic aldehyde can be used as the carbonyl component in this reaction, which can also be performed efficiently under solvent-free conditions. During this study, we discovered new compounds with moderate antitumor activities.

Supporting Information