95337-70-5Relevant academic research and scientific papers
One-pot synthesis of: N -substituted pyrroles from nitro compounds and 2,5-hexadione over a heterogeneous cobalt catalyst
Gong, Zheng,Lei, Yu,Zhou, Peng,Zhang, Zehui
, p. 10613 - 10618 (2017/10/05)
In this study, the one-pot heterocyclization of nitro compounds with 2,5-hexadione was studied for the synthesis of N-substituted pyrroles via a Paal-Knorr condensation process. The heterogeneous cobalt-nitrogen catalyst (Co-Nx/C-800-AT) was found to be active for this reaction with formic acid. Formic acid served as a hydrogen donor for the transfer hydrogenation, and also acted as an acid catalyst. More importantly, this method was tolerant of other functional groups, and hence various N-substituted pyrroles were produced with good to excellent yields. The Co-Nx/C-800-AT catalyst was highly stable, and could be reused several times without loss of its catalytic activity.
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.
