Green Synthesis of 1,4‐Dihydropyridine Derivative in Water,ChemistrySelect

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Green Synthesis of 1,4‐Dihydropyridine Derivative in Water
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-03-15 , DOI: 10.1002/slct.201800161
Shigeki Isomura ₁ , Ami Horigome ₁ , Kotaro Kubo ₁ , Yukari Yoshizawa ₁ , Yoshinori Okuno ₁ , Misaki Okayasu ₂ , Isao Azumaya ₂ , Yasuo Sato ₁

Affiliation

A simple and environmentally clean synthesis of 4‐methoxycarbonylmethyl‐1,4‐dihydropyridine‐3,5‐dicarboxylic acid dimethyl ester was achieved by heating methyl propiolate with an amine salt in water. Excess amine salt accelerated the reaction in the case of aliphatic amines, while stoichiometric amounts of propiolate ester and amine salt resulted in low yield. In the case of aniline, a 1:3 ratio of amine salt and methyl propiolate afforded 77% yield in 24 h. The free amine is proposed to serve as nucleophile for Michael addition reaction, and the liberated proton acts as an electrophilic catalyst.

中文翻译：

水中1,4-二氢吡啶衍生物的绿色合成

通过在水中加热丙炔酸甲酯和胺盐，可以简单而环保地合成4-甲氧基羰基甲基-1,4-二氢吡啶-3,5-二羧酸二甲酯。在脂族胺的情况下，过量的胺盐会加速反应，而化学计量的丙酸酯和胺盐会导致低收率。在苯胺的情况下，胺盐和丙酸甲酯的比例为1：3，在24小时内收率为77％。提出将游离胺用作迈克尔加成反应的亲核试剂，并且所释放的质子用作亲电催化剂。

更新日期：2018-03-15

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