Journal
TETRAHEDRON
Volume 69, Issue 2, Pages 738-743Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.10.082
Keywords
N-Substituted 1,4-dihydropyridines; Methyl (arylmethylidene) pyruvate; Enaminone; Zinc chloride; Dialkyl acetylenedicarboxylate; Domino Michael/cyclization
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Funding
- Alexander von Humboldt foundation
- Ministry of Health and medicinal education (Iran)
- presidential office deputy of science and technology
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An efficient one-pot synthesis of novel N-substituted 1,4-dihydropyridine derivatives via a three-component reaction of primary amines, dialkyl acetylenedicarboxylates, and methyl (arylmethylidene) pyruvates has been reported. The reaction is performed using ZnCl2 (40 mol %) in dichloroethane in good to high yields through a domino Michael/cyclization sequence. Notably, the ready availability of the starting materials, high bond-forming efficiency, good to high yields and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to N-substituted 1,4-dihydropyridines. (c) 2012 Elsevier Ltd. All rights reserved.
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