Convenient synthesis of polyfunctional dihydrothiophenes with tandem reaction of 1,3-thiazolidinedione, aldehyde, arylamine and ethyl cyanoacetate.
New, highly-functionalized dihydrothiophenes are conveniently synthesized from the novel tandem, four-component reactions of 1,3-thiazolidinedione, aldehyde, arylamine, and ethyl cyanoacetate, catalyzed by triethylamine. The reaction mechanism involves the use of Knoevenagel condensation, Michael addition, and ring-opening of 1,3-thiazolidinedione, followed by intramolecular ring closure process. The reaction is diastereoselective and only trans-2,3-dihydrothiophenes were produced in moderate yields. The functionalized dihydrothiophenes can be converted efficiently to the corresponding thiophenes by DCC dehydrogenation reaction.
Sun
Jing
J
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225002, China.
Xia
Er-Yan
EY
Yao
Rong
R
Yan
Chao-Guo
CG
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D045162:Thiazolidinediones / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
D000085:Acetates; D000447:Aldehydes; D000588:Amines; D045162:Thiazolidinediones; D013876:Thiophenes; C089946:2,4-thiazolidinedione; C007659:ethyl cyanoacetate