Dimethyl Acetylenedicarboxylate in Reactions with Substituted 3-(2-aminophenyl)-6-R-1-1,2,4-triazin-5-(2H)-ones: Structure and Properties of the Products

作者:Voskoboynik Olexii Yu*; Kovalenko Sergiy I; Okovytyy Sergiy I; Shishkina Svitlana V
来源:Journal of Heterocyclic Chemistry, 2017, 54(3): 2038-2042.
DOI:10.1002/jhet.2801

摘要

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.

  • 出版日期2017-5