Synthesis of thienopyridinones via hydrazide-alkyne cyclization

A novel and efficient method for the synthesis of thieno[3,2-c]pyridinones have been developed. The synthetic strategy relies on the synthesis of halothiophene esters utilized as substrates for subsequent Sonogashira cross-coupling reactions. Hydrazinolysis of corresponding esters and following hydr...

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Bibliographic Details
Published in:Tetrahedron 2020-05, Vol.76 (19), p.131151, Article 131151
Main Authors: Cokol, Nalan Korkmaz, Erden, Kübra, Gunay, Furkan Melih, Dengiz, Cagatay, Balci, Metin
Format: Article
Language:English
Subjects:
Alkyne cyclization
Sonogashira coupling
Thiophene
Thiophene-fused pyridinones
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Summary:A novel and efficient method for the synthesis of thieno[3,2-c]pyridinones have been developed. The synthetic strategy relies on the synthesis of halothiophene esters utilized as substrates for subsequent Sonogashira cross-coupling reactions. Hydrazinolysis of corresponding esters and following hydrazide-alkyne ring closure transformations resulted in target thienopyridinones in good yields. It is also shown that pure hydrazine monohydrate is required to facilitate the hydrazide formations. [Display omitted] •A novel and efficient method for the synthesis of thieno[3,2-c]pyridinones have been developed.•The synthetic strategy relies on the synthesis of halothiophene esters utilized as substrates for Sonogashira reactions.•The results revealed that pure hydrazine monohydrate was necessary for the formation of hydrazide intermediates.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131151