190896-00-5Relevant academic research and scientific papers
Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts
Bailen,Chinchilla,Dodsworth,Najera
, p. 9809 - 9813 (2000)
S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium tetrafluoroborate (TOTT) and hexafluorophosphate (HOTT) are cheap and convenient reagents for the rapid and high-yielding preparation of primary amides when reacted with carboxylic acids and ammonium chloride in the presence of diisopropylethylamine. The reaction is chemoselective and undesired ammonolysis of other sensitive functional groups is not observed. (C) 2000 Elsevier Science Ltd.
(E)-5-Tosyl-4-pentenamide: A vinyl sulfone for the one-pot general synthesis of indolizidine derivatives
Caturla, Francisco,Najera, Carmen
, p. 3789 - 3792 (2007/10/03)
(E)-5-tosyl-4-pentenamide (3), easily prepared from 4-pentenoic acid by stereoselective iodosulfonylation-dehydroiodination and further amidation with oxalyl chloride and ammonia reacts with sodium hydride at room temperature in DMF and then with 1,3-dielectrophiles such as 1,3-dihalides and α,β-unsaturaled esters to provide stereoselectively differently substituted indolizidines 6.
