2-氨基-4,5-二氢噻吩-3-腈：一种新的合成方法、量子化学研究以及生成新型六氢噻吩并[2,3-d]嘧啶的曼尼希型反应。

2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines.

作者信息

Dotsenko Victor V, Bespalov Alexander V, Vashurin Arthur S, Aksenov Nicolai A, Aksenova Inna V, Chigorina Elena A, Krivokolysko Sergey G

机构信息

Kuban State University, Department of Chemistry & High Technologies, 149 Stavropolskaya st., Krasnodar 350040, Russian Federation.

North Caucasus Federal University, Department of Organic Chemistry, 1 Pushkina st., Stavropol 355009, Russian Federation.

出版信息

ACS Omega. 2021 Nov 19;6(48):32571-32588. doi: 10.1021/acsomega.1c04141. eCollection 2021 Dec 7.

-2-Amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles were prepared either by the reaction of 3-aryl-2-cyanothioacrylamides with α-thiocyanatoacetophenone or by the Michael-type addition of cyanothioacetamide to α-bromochalcones followed by intramolecular cyclization. The mechanism of the first reaction was studied using high-level quantum chemical calculations. Density functional theory (DFT) studies were carried out to determine the mechanism of the first reaction. A new approach toward the construction of the thieno[2,3-d]pyrimidine core system was demonstrated by the reaction of the prepared dihydrothiophenes with HCHO and RNH under noncatalyzed Mannich conditions.