Journal of Siberian Federal University. Chemistry / Application of 3,4-Dihydropyrimidine-2(1H)-thiones as Bifunctional S, N-Nucleophiles in the Reaction with 4,5-Dichlorophthalonitrile

Full text (.pdf)
Issue
Journal of Siberian Federal University. Chemistry. 2025 18 (2)
Authors
Baklagin, Vyacheslav L.; Bukhalin, Vladimir V.; Makarova, Elena S.; Abramov, Igor G.; Ivanovsky, Sergey. A.
Contact information
Baklagin, Vyacheslav L.: Yaroslavl State Technical University Yaroslavl, Russian Federation; ; Bukhalin, Vladimir V. : Yaroslavl State Technical University Yaroslavl, Russian Federation; Makarova, Elena S.: Yaroslavl State Technical University Yaroslavl, Russian Federation; Abramov, Igor G. : Yaroslavl State Technical University Yaroslavl, Russian Federation; Ivanovsky, Sergey. A.: Yaroslavl State Pedagogical University named after K. D. Ushinsky Center for Transfer of Pharmaceutical Technologies Yaroslavl, Russian Federation
Keywords
aromatic nucleophilic substitution; benzo[4,5]thiazolo[3,2- a]pyrimidines; 4,5-dichlorophthalonitrile; 3,4-dihydropyrimidine-2(1H)-thiones
Abstract

By activated aromatic substitution reaction between 4,5-dichlorophthalonitrile and 3,4-dihydropyrimidine-2(1H)-thiones the corresponding benzo[4,5]thiazolo[3,2-a]pyrimidines were synthesized. Carrying out the reaction in DMF in the presence of K2CO3 or triethylamine allowed to obtain the target products in yields up to 52 %. The use of triethylamine as a base made it possible to chemoselectively obtain the thiazole ring in a reaction with dihydropyrimidine-2-thione containing hydroxyl groups in the aryl substituent

Pages
173–182
EDN
YVOHHR
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/156207