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Dimethyl Acetylenedicarboxylate in Reactions with Substituted 3‐(2‐aminophenyl)‐6‐R 1 ‐1,2,4‐triazin‐5‐(2 H )‐ones: Structure and Properties of the Products
Author(s) -
Voskoboynik Olexii Yu.,
Кovalenko Sergiy I.,
Okovytyy Sergiy I.,
Shishkina Svitlana V.
Publication year - 2017
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.2801
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , hydrazine (antidepressant) , reagent , nucleophile , ring (chemistry) , pyrimidine , hydrolysis , acetylenedicarboxylate , medicinal chemistry , organic chemistry , stereochemistry , cycloaddition , catalysis , chromatography
The article describes unusual [5 + 1]‐cyclocondensations of dimethyl acetylenedicarboxylate (DMAD), in which this reagent uncharacteristically acts as a 1,1‐biselelectrophilic agent. Reactions of DMAD with 1,5‐bisnucleophilic 3‐(2‐aminophenyl)‐6‐R 1 ‐1,2,4‐triazin‐5(2H)‐ones yielded triazinoquinazoline‐derived diesters. The latter was shown to react with nucleophiles: hydrazine cleaved the pyrimidine ring of the diesters to give anilines, while ester hydrolysis furnished corresponding carboxylic acids.