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S N Ar versus Buchwald–Hartwig Amination/Amidation in the Imidazo[2,1‐ b ][1,3,4]thiadiazole Series
Author(s) -
Copin Chloé,
Massip Stéphane,
Léger JeanMichel,
Jarry Christian,
Buron Frédéric,
Routier Sylvain
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500977
Subject(s) - amination , chemistry , palladium , microwave irradiation , derivative (finance) , medicinal chemistry , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , financial economics , economics
An original and efficient palladium‐catalyzed amination of imidazo[2,1‐ b ][1,3,4]thiadiazole is reported. The S N Ar 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 S N Ar 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.