83756-25-6Relevant articles and documents
Protection of Primary Amines as N-Substituted 2,5-Dimethylpyrroles
Bruekelman, Stephen P.,Leach, (Miss) Susan E.,Meakins, G. Denis,Tirel, Malcolm D.
, p. 2801 - 2807 (2007/10/02)
Protection of primary amine group is achieved by incorporating it into an N-substituted 2,5-dimethylpyrrole system.The method affords protection against strong bases and nucleophiles, heating with concentrated alkali, standard mineral acid work-up conditions, and various other reagents.Phenyl-, pyridil-, thiazolyl-, and alkyl-amines have been studied.All give trisubstituted pyrroles in high yield (>80percent) by reaction with hexane-2,5-dione.The pyrroles from the first three types are stable to storage; even the N-alkyl compounds can be used without difficulty.Regeneration of the amine group, by treatment with hydrxylamine hydrochloride, is efficient (80percent yield) with the phenyl, pyridyl, and alkyl compounds but less satisfactory (60 - 65percent generally but down to 25percent in two cases) with the thiazolyl derivatives.
