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Protecting Group Free Synthesis of Carboxyl‐substituted Dihydropyrimidines Through Biginelli Reaction
Author(s) -
Ostapchuk Eugeniy N.,
Plaskon Andrey S.,
Grygorenko Oleksandr O.,
Tolmachev Andrey A.,
Ryabukhin Sergey V.
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1568
Subject(s) - chemistry , biginelli reaction , group (periodic table) , organic chemistry , stereochemistry , catalysis
Chlorotrimethylsilane‐promoted Biginelli‐type reaction of benzaldehyde, acetoacetic acid derivatives, and various carboxyl‐containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono‐substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one‐pot, protecting group free synthesis of dihydropyrimidines possessing carboxylic functionality.