Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles

Tzu Ting Kao, Bo Kai Peng, Min Chieh Liang, Chia Jui Lee, I. Chia Chen, Kak Shan Shia*, Yen-Ku Wu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Making use of temperature-controlled thiation as a key operation, a simple route to 2-aminothiophenes or thieno[2,3-c]isothiazoles has been newly developed wherein the 2-aminothiophene nucleus was formed through an initial formation of thioamide followed by a 5-exo-dig addition to the tethered alkyne; however, under harsher thermal conditions, excess sulfur-transferring reagents enabled further oxidative thiation to generate the corresponding thieno[2,3-c]isothiazoles.

Original languageEnglish
Pages (from-to)14688-14697
Number of pages10
JournalJournal of Organic Chemistry
Volume83
Issue number23
DOIs
StatePublished - 7 Dec 2018

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