Mesoporous Niobium Oxide Spheres as an Effective Catalyst for the Transamidation of Primary Amides with Amines

Abstract

Mesoporous niobium oxide spheres (MNOS), conveniently prepared by a novel antisolvent precipitation approach, have been shown to be an effective catalyst for the transamidation of primary amides with amines. This novel transamidation can be efficiently carried out under solvent-free conditions and is applicable to a wide range of primary amides and amines to provide N-alkyl amides in good to excellent yields. The catalyst is highly stable and reusable. The application of this transamidation reaction has been demonstrated in the synthesis of antidepressant drug moclobemide and other druglike compounds.

Lewis Acid Catalysis of Nb2O5 for Reactions of Carboxylic Acid Derivatives in the Presence of Basic Inhibitors

“…5–8), (3) dehydration reactions of alcohols and polyols (No. 9–16),, (4) nucleophilic substitution reactions of carboxylic acids (and their derivatives),, and (6) selective oxidation/dehydrogenation reactions …”

“…[5][6][7][8], [12][13][14][15][16][17] (3) dehydration reactions of alcohols and polyols (No. [9][10][11][12][13][14][15][16], [15,[18][19][20][21][22][23][24][25][26][27][28][29] (4) nucleophilic substitution reactions of carboxylic acids (and their derivatives), [15,[30][31][32][33][34][35][36][37][38] and (6) selective oxidation/ dehydrogenation reactions. [39][40][41][42][43][44] The hydration reactions of alkenes (No.…”

“…25) reported by Chen et al have also been classified as nucleophilic substitution reactions of carboxylic acids derivatives catalyzed by Nb 2 O 5 . [38] Moreover, Nb 2 O 5 has been used for selective oxidations (No. 26,30), [39,43] photocatalytic oxidations (No.…”

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

“…Alternatively, enzymatic transamidation was reported, but it suffers from some drawbacks such as limited functional group tolerance and long reaction time. To overcome these detriments new homogeneous like Sc(OTf) 3 , Fe‐H 2 O, Cu(OAc) 2 , hypervalent iodine, Nb 2 O 5 spheres, ionic liquid, Pd(OAc) 2 , K 2 S 2 O 8 and heterogeneous catalysts such as Poly DMAP‐Based hafnium Chloride and montmorillonite KSF, cerium(III) immobilised on aminatedepichlorohydrin‐activated agarose matrix (CAEA), sulfated tungstate, CeO 2 , Fe‐mont, MnO 2 are reported. Microwave irradiation as well as catalyzed transamidation reaction .…”

Colloid and nano-sized catalysts in organic synthesis: X. Synthesis of carboxamides by direct amidation of carboxylic acids and transamidation catalyzed by colloid copper

“…In the case of lower amides the reaction was performed at temperature below 30°C [29]. An effective catalyst for primary amides transamidation occurred to be mesoporous spheres of niobium oxide [30]. Reaction of various primary amides with wide range of amines was effectively catalyzed by cerium oxide at 160°C with the formation of the corresponding N-alkylamides in solvent-free conditions [31].…”