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

Carlos A. M. Figueiredo; K. R. Kishore K. Reddy; Paula A. Monteiro; João E. de Carvalho; Ana L. T. G. Ruiz; Luiz F. Silva Jr

doi:10.1055/s-0032-1318478

Synthesis, Table of Contents

Synthesis 2013; 45(8): 1076-1082
DOI: 10.1055/s-0032-1318478

paper

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

Carlos A. M. Figueiredo

^aInstituto 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

^aInstituto 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

^bDivisão de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, 13083-970 Campinas, SP, Brazil

,

João E. de Carvalho

^bDivisão 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

^bDivisão de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, 13083-970 Campinas, SP, Brazil

,

Luiz F. Silva Jr*

^aInstituto 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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Abstract

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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.

Key words

cyclizations - iodine - catalysis - heterocycles - amines - aldehydes - antitumor agents

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References

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