Microwave-Assisted Combinatorial Synthesis of Hexa-Substituted 1,4-Dihydropyridines Scaffolds Using One-Pot Two-Step Multicomponent Reaction followed by a S-Alkylation

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• 作者：Ming Li ; Zhengquan Zuo ; Lirong Wen ; Shuwen Wang
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2008
• 出版时间：May 2008
• 年：2008
• 卷：10
• 期：3
• 页码：436 - 441
• 全文大小：124K
• 年卷期：v.10,no.3(May 2008)
• ISSN：1520-4774

文摘

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 β-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.