Synthesis of 4-(trifluoromethyl)thiocoumarins.

Autor: Golubev, A. S., Golubev, I. M., Ostapchuk, P. N., Strelkova, T. V., Suponitsky, K. Yu., Chkanikov, N. D.
Zdroj: Russian Chemical Bulletin; Oct2024, Vol. 73 Issue 10, p3045-3054, 10p
Abstrakt: A convenient method for the synthesis of poorly studied 4-(trifluoromethyl)thiocoumarins from 1-[2-(tert-butylthio)phenyl]-2,2,2-trifluoroethanones was developed. Thiopyranone core of 4-(trifluoromethyl)thiocoumarins was constructed by S-acylation of 1-[2-(tert-butylthio)phenyl]-2,2,2-trifluoroethanones with bromoacetyl bromide followed by treatment with triphenylphosphine to give the phosphonium salt and subsequent intramolecular Wittig reaction. S-Acylation of these substrates with acetyl chlorides bearing active methylene group and subsequent intramolecular Knövenagel condensation gave 3-substituted 4-(trifluoromethyl)thiocoumarins. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index