Microwave-assisted combinatorial synthesis of hexa-substituted 1,4-dihydropyridines scaffolds using one-pot two-step multicomponent reaction followed by a S-alkylation

Journal of Combinatorial Chemistry
Ming LiShu-Wen Wang

Abstract

A sequential one-pot two-step protocol for microwave-assisted synthesis of Hantzsch-type hexa-substituted 1,4-dihydropyridines has been developed. The three-component reactions of beta-aroylthioamides with aldehydes and acetonitrile derivatives produce the intermediates in situ followed by a S-alkylation to afford hexa-substituted 1,4-dihydropyridines. The reaction presumably proceeds via a Knoevenagel condensation-Michael addition-cyclocondensation-rearrangement-S N2 reaction sequence. Target compounds were obtained in high yields and simply purified by recrystallization. The novel method is complementary to the classical Hantzsch synthesis in that it is well-suited to the preparation of hexa-substituted 1,4-dihydropyridines.

References

Jul 10, 1999·Carbohydrate Research·X M ChenZ T Huang
Oct 12, 2000·Angewandte Chemie·A Dömling, I Ugi
Nov 10, 2000·Carbohydrate Research·X M ChenZ T Huang
Jul 11, 2002·Journal of the American Chemical Society·Shinji Yamada, Chisako Morita
Nov 6, 2004·The Journal of Organic Chemistry·Lal Dhar S Yadav, Ritu Kapoor
Nov 24, 2004·Angewandte Chemie·C Oliver Kappe
Jan 11, 2005·Journal of Combinatorial Chemistry·Inés CarrancoRodolfo Lavilla
Feb 19, 2005·Angewandte Chemie·Diego J Ramón, Miguel Yus
Mar 31, 2005·Journal of the American Chemical Society·Xihe BiBing Li
Nov 5, 2005·The Journal of Organic Chemistry·S PeruncheralathanH Junjappa
Feb 25, 2006·The Journal of Organic Chemistry·Elisa FasaniAngelo Albini
Mar 15, 2006·Journal of Combinatorial Chemistry·Wong-Jin ChangChung-Ming Sun
May 22, 2007·European Journal of Pharmacology·Rachel W S LiGeorge P H Leung

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Citations

Dec 24, 2014·Organic & Biomolecular Chemistry·Wei-Si GuoMing Li
Dec 25, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Helmut M Hügel
Apr 22, 2009·Molecular Diversity·C Oliver Kappe, Doris Dallinger
Mar 9, 2021·Organic & Biomolecular Chemistry· Preeti, Krishna Nand Singh
Jan 14, 2010·Journal of Combinatorial Chemistry·Xiang-Shan WangShu-Jiang Tu

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