Synthesis of polysubstituted 1,4-dihydropyridines via three-component reaction

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 goo...

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Veröffentlicht in:Tetrahedron 2013-01, Vol.69 (2), p.738-743
Hauptverfasser: Balalaie, Saeed, Baoosi, Leila, Tahoori, Fatemeh, Rominger, Frank, Bijanzadeh, Hamid Reza
Format: Artikel
Sprache:eng
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Zusammenfassung: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.10.082