The reaction of thioesters with nitriles. A new synthetic approach to the preparation of substituted 4-alkylthio-and 4-arylthiopyrimidine derivatives
A Herrera, R Martı́nez-Alvarez, P Ramiro
Index: Herrera, Antonio; Martinez-Alvarez, Roberto; Ramiro, Pedro Tetrahedron, 2003 , vol. 59, # 37 p. 7331 - 7336
Full Text: HTML
Citation Number: 5
Abstract
S-Alkyl and S-aryl thioesters react with nitriles in the presence of triflic anhydride to form substituted 4-alkylthio-and 4-arylthiopyrimidines. However, when methyl thiocyanate is used as nitrile, dithioimidocarbonates are formed. A mechanism to explain these differences is postulated.
Related Articles:
An Attempted Fries Reaction with Thiolesters. The Formation of Trithioörthoesters1
[Tarbell; Herz Journal of the American Chemical Society, 1953 , vol. 75, p. 1668,1670]
[Cohen,T. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 25 p. 4744 - 4746]
Anhydrous hydrogen fluoride catalyzed Friedel-Crafts reactions of thioaromatic compounds
[Aslam, Mohammad; Davenport, Kenneth G.; Stansbury, Wayne F. Journal of Organic Chemistry, 1991 , vol. 56, # 20 p. 5955 - 5958]
An Attempted Fries Reaction with Thiolesters. The Formation of Trithioörthoesters1
[Tarbell; Herz Journal of the American Chemical Society, 1953 , vol. 75, p. 1668,1670]
Carbanion-Bildung aus Estern der Orthothiokohlensäure durch nukleophile Substitution an Schwefel
[Wildschut,G.A. et al. Monatshefte fuer Chemie, 1967 , vol. 98, p. 1043 - 1049]