Ionic liquid catalyzed one-pot multi-component synthesis of fusedpyridine derivatives:A strategyfor green and sustainable chemistry

被引:18
|
作者
Jadhav, Chetan K. [1 ]
Nipate, Amol S. [1 ]
Chate, Asha V. [1 ]
Patil, Anil P. [2 ]
Gill, Charansingh. H. [1 ]
机构
[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, Maharashtra, India
[2] Inst Microbial Technol IMTECH, Chandigarh, India
关键词
ACTIVE METHYLENE-COMPOUNDS; MICHAEL ADDITION; PERFECT SYNERGY; PYRIDINE; SOLVENTS;
D O I
10.1002/jhet.4135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a combinatorial library of heterocycle-fused pyridine derivatives has been achieved successfully via a one-pot four-component reaction of aromatic/aliphatic aldehyde, malononitrile, thiazolidine-2,4-dione and ammonium acetate in the presence of piperidinium acetate as the catalyst. It involved the Knoevenagel condensation of the aldehyde and malononitrile to produce arylidene malononitrile as an intermediate, which was further intramolecular cyclization through Michael type addition ketone to the electrophilic double bond of the arylidene to produce fused pyridines in high yields. Environmental friendliness, low cost, Operational simplicity, extensive reusability and applicability, and easy recovery of the catalyst using simple evaporation are the critical features of this methodology. Also, a series of pyridine based dihydrothiazolo[4,5-b] pyridine-6-carbonitrile analogs were synthesized and selected for their in vitro antifungal and antibacterial activities.
引用
收藏
页码:4291 / 4303
页数:13
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