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Synthesis 2004(10): 1595-1600  
DOI: 10.1055/s-2004-822409
PAPER
© Georg Thieme Verlag Stuttgart · New York

Hexamethylenetetramine as a Cheap and Convenient Alternative Catalyst in the Baylis-Hillman Reaction: Synthesis of Aromatic Compounds with Anti-Malarial Activity

R. O. M. A. de Souzaa, Bruno A. Meirelesa, Lúcia C. S. Aguiarb, M. L. A. A. Vasconcellos*a
a Lab. H0-027, Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Bloco H, CCS, Ilha do Fundão, Rio de Janeiro, RJ, Brazil
Fax: +55(21)22702683; e-Mail: mlaav@nppn.ufrj.br;
b Lab. H1-029, Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Bloco H, CCS, Ilha do Fundão, Rio de Janeiro, RJ, Brazil
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Publication History

Received 5 February 2004
Publication Date:
16 June 2004 (online)

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Abstract

Hexamethylenetetramine (7, HMT) is a cheap alternative catalyst in the Baylis-Hillman reaction between aromatic aldehydes and methyl acrylate or acrylonitrile. The use of 0.1 equiv or 1.0 equiv of HMT proved to be an efficient catalyst for the preparation of 1, 8a-c,h, 9a-c and 10 in good to high yieds. The Baylis-Hillman adducts 9c and 10 show high potency against P. falciparum in vitro (anti-malarial activity), and new compounds 9f,h,i are also efficiently prepared using our methodology.

KeyWords

nucleophilic additions - aldehydes - amines - catalysis - drugs