Ionic liquid promoted preparation of 4H-thiopyran and pyrimidine nucleoside-thiopyran hybrids through one-pot multi-component reaction of thioamide.
One-pot multi-component reactions of aldehydes, cyanothioacetamide and malononitrile promoted by ionic liquid proved to be an efficient way for the synthesis of thiopyran derivatives. Without any added catalyst, both aromatic and aliphatic aldehydes participated in this reaction smoothly. As an application of this method, a pyrimidine nucleoside-thiopyran chimera with potential biological activities was obtained in high yield from 5-formyl-2'-deoxyuridine. In addition, the ionic liquid used can be easily recovered and effectively reused for at least 5 times.
Zhang
Xinying
X
Henan Key Laboratory for Environmental Pollution Control, School of Chemistry and Environmental Sciences, Henan Normal University, Xinxiang, Henan, 453007, People's Republic of China. xyzh518@sohu.com
Li
Xiaoyan
X
Fan
Xuesen
X
Wang
Xia
X
Li
Dongfang
D
Qu
Guirong
G
Wang
Jianji
J
D000447:Aldehydes / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013853:Thioacetamide / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*
D000447:Aldehydes; D052578:Ionic Liquids; D009570:Nitriles; D011714:Pyrans; D011743:Pyrimidines; D013438:Sulfhydryl Compounds; D013854:Thioamides; C522033:thiopyran; D013853:Thioacetamide; C000945:dicyanmethane; C030986:pyrimidine