Molecular Diversity 2011-02-01

Convenient synthesis of polyfunctional dihydrothiophenes with tandem reaction of 1,3-thiazolidinedione, aldehyde, arylamine and ethyl cyanoacetate.

Jing Sun, Er-Yan Xia, Rong Yao, Chao-Guo Yan

Index: Mol. Divers. 15(1) , 115-23, (2011)

Full Text: HTML

Abstract

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.

Related Compounds

  • Ethyl cyanoacetate

Related Articles:

Self-assembled hybrid metal oxide base catalysts prepared by simply mixing with organic modifiers.

2015-01-01

[Nat. Commun. 6 , 8580, (2015)]

Intramolecular Hydrogen Bonding and Linear Pentapyrrole Conformation.

2014-08-01

[Monatsh. Chem 145(7) , 1117-1135, (2014)]

Microwave-assisted and efficient solvent-free knoevenagel condensation. A sustainable protocol using porous calcium hydroxyapatite as catalyst.

2010-02-01

[Molecules 15(2) , 813-23, (2010)]

Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions.

2000-03-10

[J. Org. Chem. 65(5) , 1359-65, (2000)]

Direct organocatalytic and highly enantio- and diastereoselective Mannich reactions of alpha-substituted alpha-cyanoacetates.

2005-05-06

[Angew. Chem. Int. Ed. Engl. 44(19) , 2896-9, (2005)]

More Articles...