39677-42-4

Upstream product

• 116170-90-2 3-amino-4-cyano-5-(methylthio)thiophene-2-carboxylic acid ethyl ester 
• 5147-80-8 [Bis(methylthio)methylene]malononitrile 

Relevant academic research and scientific papers

Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via carbon-sulfur bond activation: A new avenue to homocoupling reactions

The Pd-catalyzed, CN-directed unsymmetrical synthesis of 2,4′-bithiophenes via an unprecedented homocoupling reaction is described. The NH2/CN/SMe arrangement breaks the routine. The cooperative performance of the functional groups in thiophenes would open up a new vision in the field of metal catalysis homocoupling reactions by joining the electrophilic and nucleophilic motifs of the substrate. Furthermore, it is found that the α-chelating effect of the carbonyl group in amino thiophene offers a new class of synthetic protocols for C-N cross-coupling with arylboronic acids. The bidentate N,O-chelation provides a series of advantages such as copper-catalyzed, ligand- and base-free under open-flask conditions. Interestingly, the combination of the C-N cross-coupling/homocoupling reactions in a domino fashion led to the bithiophene adducts featuring the C(Ar)-N bond cleavage in the nitrogen that bridged between the two thiophene units.

Reactions of ketene dithioacetal for a new versatile synthesis of 4,5-substituted 3-aminothiophene-2-carboxylate derivatives

ABSTRACT: Poly substituted 3-aminothiophenes were successfully synthesized in good yields by using a one-pot protocol via ketene S,S-acetal as an intermediate in basic medium (K2CO3/N,N-dimethylformamide) followed by Dieckmann condensation with ethyl bromoacetate. Further, chemistry of thiophenes was explored using active functional groups such as C3–NH2, C4–CN and C5–SCH3 on the thiophene nucleus. Synthesis of ethyl 3-acetamido-4-cyano-5-(methylthio)thiophene-2-carboxylate derivatives and ethyl 3-amino-4-carbamoyl-5-(methylthio)thiophene-2-carboxylate derivatives.