Synthesis of New Thienopyridine Derivatives by a Reaction of 4‐(Methylsulfanyl)‐6,7‐dihydrothieno[3,2‐c]pyridine with Amino Acids

Abstract

New thienopyridine derivatives were synthesized by the reaction of 4-(methylsulfanyl)-6,7dihydrothieno [3,2-c]pyridine (5) with amino acids. The use of β-amino acids led to thienopyridopyrimidone derivatives (9a-g). Using α-amino acids, such as glycine and racemic alanine under the same reaction conditions, compounds with two thienopyridine units were obtained. The structure of the novel compounds was confirmed by IR, 13 C, and 1 H NMR spectroscopy, as well as mass spectrometry, along with single crystal X-ray analysis. C 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:124-130, 2013; View this article online at wileyonlinelibrary.com.

Synthesis of Dihydrothienopyridine Derivatives Fused with Triazole Rings

“…However, no reaction was observed between compound 5 and acetic hydrazide ( 7b ) in boiling butanol. Therefore to convert the thione ( 5 ) to a more reactive species, it was S ‐alkylated with methyl iodide to form 4‐(methylsulfanyl)‐6,7‐dihydrothieno[3,2‐ c ]pyridine ( 6 ) (Scheme ). The methylation was carried out in acetonitrile/dichloromethane at 26°C in the presence of Cs 2 CO 3 .…”

“…In our previous study, the [3+2] and [2+2] cycloadditions , as well as cyclocondensation reactions , were investigated to synthesize novel fused conformationally constrained thienopyridines.…”