908075-41-2Relevant academic research and scientific papers
SNAr versus Buchwald-Hartwig Amination/Amidation in the Imidazo[2,1-b][1,3,4]thiadiazole Series
Copin, Chloé,Massip, Stéphane,Léger, Jean-Michel,Jarry, Christian,Buron, Frédéric,Routier, Sylvain
, p. 6932 - 6942 (2015)
An original and efficient palladium-catalyzed amination of imidazo[2,1-b][1,3,4]thiadiazole is reported. The SNAr and Buchwald-Hartwig cross-coupling reactions were investigated to access C-2 aminated imidazo[1,2-b][1,3,4]thiadiazole derivatives. The reaction conditions were optimized under microwave irradiation, and a wide range of amines were used to determine the scope and limitations of the method. To complete this study, the palladium-catalyzed and SNAr amination reactions were compared to determine the best strategy. The X-ray crystallographic data of imidazo[2,1-b][1,3,4]thiadiazole derivative 20 was used to formally establish the structures of the products. An efficient and convenient method has been developed for the preparation of C-2 aminated imidazo[1,2-b][1,3,4]thiadiazole derivatives by using SNAr or Buchwald-Hartwig reactions. The process was highly compatible with various functional groups and afforded the final compounds in very good yields.
Synthesis and properties of (6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-3- pyrimidinyl)acetic acid methyl ester
Kukaniev,Rakhmonov,Safarov,Khodzhibaev,Osimov
, p. 499 - 502 (2008/12/21)
2-amino-5-bromo-1,3,4-thiadiazole, 2-bromo-6-phenyl-imidazo[2,1-b]-1,3,4- thiadiazole, 2,5-dibromo-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole, 2-morpholino-5-morpholinomethyl-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole.
