857349-72-5Relevant articles and documents
Alpha-oxidation of amine derivatives by bis(2,2,2-tri-chloroethyl) azodicarboxylate and application of its products as iminium ion equivalents
Honzawa, Shinobu,Uchida, Mitsuaki,Tashiro, Takuya,Sugihara, Takumichi
, p. 994 - 1029 (2017/07/27)
Alpha-oxidation of amine derivatives by azodicarboxylate was examined. Among several azodicarboxylate esters and amides tested, bis(2,2,2-trichloroethyl) azodicarboxylate, that has highly electrophilic 2,2,2-trichloroethoxycarbonyl functional groups, was found to have excellent oxidation reactivity. Acylated or carbamoylated amines were suitable substrates for this reaction condition. Tertially amines could react in the same manner, but spontaneous elimination of hydrazinyl group occurred to give dimerized products. The reaction products were found to react with nucleophiles in the presence of Lewis or Br?nsted acid catalyst. This strongly suggests that the reaction products, alpha-hydrazinated amine derivatives, might serve as carbonyl group equivalents, very useful intermediates in synthetic organic chemistry.
An efficient sequence for the preparation of small secondary amine hydrochloride salts for focused library generation without need for distillation or chromatographic purification
Dubowchik, Gene M.,Michne, Jodi A.,Zuev, Dmitry
, p. 3147 - 3149 (2007/10/03)
Collections of small secondary amines for compound library generation can be efficiently prepared by amide reduction using BH3-THF or Red-Al followed by brief methanolysis, trapping with di-tert-butyl dicarbonate, and deprotection with 4M HCl i
