Journal
TETRAHEDRON LETTERS
Volume 52, Issue 27, Pages 3455-3459Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.04.098
Keywords
Sequential multicomponent reactions; Dihydropyridines; Imino-Diels-Alder reactions; Substituted naphthyridines
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Funding
- UGC, New Delhi, India
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Facile and efficient synthesis of tetrasubstituted 1,4- and 1,6-dihydropyridines (DHPs) has been achieved by employing three-component domino reaction using dimethyl acetylenedicarboxylate (DMAD), aliphatic amines, and alpha,beta-unsaturated aldehyde in the presence of 30 mol % trifluoroacetic acid. Interestingly, regioselectivity for the synthesis of 1,4-dihydropyridines can be increased by using 30 mol % triflic acid. In addition, the synthesis of fused-naphthyridine derivatives has been accomplished involving imino-Diels-Alder reaction by employing 1,4-dihydropyridines, aromatic aldehydes, and aromatic amines. (C) 2011 Published by Elsevier Ltd.
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