Microwave-assisted combinatorial synthesis of hexa-substituted 1,4-dihydropyridines scaffolds using one-pot two-step multicomponent reaction followed by a S-alkylation.
A sequential one-pot two-step protocol for microwave-assisted synthesis of Hantzsch-type hexa-substituted 1,4-dihydropyridines has been developed. The three-component reactions of beta-aroylthioamides with aldehydes and acetonitrile derivatives produce the intermediates in situ followed by a S-alkylation to afford hexa-substituted 1,4-dihydropyridines. The reaction presumably proceeds via a Knoevenagel condensation-Michael addition-cyclocondensation-rearrangement-S N2 reaction sequence. Target compounds were obtained in high yields and simply purified by recrystallization. The novel method is complementary to the classical Hantzsch synthesis in that it is well-suited to the preparation of hexa-substituted 1,4-dihydropyridines.
Li
Ming
M
Key Laboratory of Eco-Chemical Engineering, Ministry of Education, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China. liming928@qust.edu.cn
Zuo
Zhengquan
Z
Wen
Lirong
L
Wang
Shuwen
S
D000478:Alkylation; D020650:Combinatorial Chemistry Techniques; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
D004095:Dihydropyridines; C038806:1,4-dihydropyridine