83697-65-8Relevant academic research and scientific papers
Chemoselective acylation of primary amines and amides with potassium acyltrifluoroborates under acidic conditions
Galvez, Alberto Osuna,Schaack, Cedric P.,Noda, Hidetoshi,Bode, Jeffrey W.
supporting information, p. 1826 - 1829 (2017/02/15)
Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.
Solid phase synthesis of amides using Mukaiyama's reagent
Tao, Bin,Boykin, David W.
, p. 10 - 11 (2007/10/03)
A new solid-phase synthetic method using Mukaiyama's reagent under mild conditions is reported to prepare amides in high purity without purification after cleavage from the resins.
5,6-DIHYDROPHENANTHRIDIN-5-YL AS AN ACTIVATABLE PROTECTING GROUP OF CARBOXYLIC ACID - A DIRECT PREPARATION OF AMIDES FROM 5-ACYL-5,6-DIHYDROPHENANTHRIDINE
Narasaka, Koichi,Hirose, Takuji,Uchimaru, Tadafumi,Mukaiyama, Teruaki
, p. 991 - 992 (2007/10/02)
Various amides are directly prepared from the protected carboxylic acids, 5-acyl-5,6-dihydrophenanthridines, by the reaction with primary amines in the presence of ceric pyridinium chloride and cupric oxide.
