jo8b01866_si_001.pdf (8.07 MB)
Temperature-Controlled Thiation of α‑Cyano-β-Alkynyl Carbonyl Derivatives for De Novo Synthesis of 2‑Aminothiophenes and Thieno[2,3‑c]isothiazoles
Version 2 2022-05-06, 19:13
Version 1 2018-10-12, 17:20
journal contribution
posted on 2018-10-02, 00:00 authored by Tzu-Ting Kao, Bo-Kai Peng, Min-Chieh Liang, Chia-Jui Lee, I-Chia Chen, Kak-Shan Shia, Yen-Ku WuMaking
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.