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Atropisomerism in N 1‐aryl Substituted 3,4‐dihydropyrimidin‐2(1H)‐thiones
Author(s) -
Gonçalves Itamar L.,
Davi Leonardo,
Machado das Neves Gustavo,
Porto Kagami Luciano,
Garcia Solange C.,
Oliveira Battastini Ana M.,
Figueiró Fabrício,
Faria Santos Canto Rômulo,
Merlo Aloir A.,
EiflerLima Vera L.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003229
Subject(s) - atropisomer , chemistry , substituent , aryl , ring (chemistry) , chirality (physics) , selectivity , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , alkyl
Dihydropyrimidinone/thiones (DHPMs) are heterocycles widely explored due to their ability to interact with different pharmacological targets. We report herein the C–N axial chirality in a DHPM scaffold with the presence of various substituents at the ortho ‐position of the aromatic ring linked to the N1. This structural feature produced atropisomerism due to the restricted rotation around the C−N bond. The atropisomerism in DHPMs was investigated by NMR, HPLC, and in silico experiments. The effect of the solvent, microwave radiation, temperature, and substituent at the ortho position on the selectivity of the reaction was examined.