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Green Synthesis of 1,4‐Dihydropyridine Derivative in Water
Author(s) -
Isomura Shigeki,
Horigome Ami,
Kubo Kotaro,
Yoshizawa Yukari,
Okuno Yoshinori,
Okayasu Misaki,
Azumaya Isao,
Sato Yasuo
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800161
Subject(s) - aniline , chemistry , amine gas treating , yield (engineering) , salt (chemistry) , nucleophile , electrophile , catalysis , stoichiometry , organic chemistry , medicinal chemistry , derivative (finance) , materials science , economics , financial economics , metallurgy
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.