1864-93-3Relevant articles and documents
Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles
Senthamarai, Thirusangumurugan,Murugesan, Kathiravan,Natte, Kishore,Kalevaru, Narayana V.,Neumann, Helfried,Kamer, Paul C. J.,Jagadeesh, Rajenahally V.
, p. 1235 - 1240 (2018/02/09)
N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.
Silver(I)-mediated regioselective oxidative cross-coupling of phenol and aniline derivatives resulting in 2′-aminobiphenyl-2-ols
Berkessa, Sololiya C.,Clarke, Zachary J.F.,Fotie, Jean,Bohle, D. Scott,Grimm, Casey C.
supporting information, p. 1613 - 1618 (2018/03/29)
A broad and efficient regioselective aerobic oxidative cross-coupling of phenols and aniline derivatives in the presence of AgNO3 and H2O2 resulting in 2′-aminobiphenyl-2-ols has been developed. This reaction is selective toward the creation of a new C–C bond at the ortho position to both amine and hydroxyl functional groups in the respective starting materials. Although oxidative cross-coupling of phenols and anilines resulting in 2′-aminobiphenyl-2-ol derivatives have been reported, these reactions have been mainly limited to 2-naphthol and 1-naphthol. This is one of the rare reports in which this type of cross-coupling reaction is expanded to simple phenol derivatives.
Catalyst-free one-pot reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids using sodium borohydride in 2,2,2-trifluoroethanol
Tajbakhsh, Mahmood,Hosseinzadeh, Rahman,Alinezhad, Heshmatollah,Ghahari, Somayeh,Heydari, Akbar,Khaksar, Samad
experimental part, p. 490 - 496 (2011/03/20)
A simple and convenient procedure for the reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids is described using sodium borohydride as a reducing agent in 2,2,2- trifluoroethanol without use of a catalyst or any other additive. The solvent can be readily recovered from reaction products in excellent purity for direct reuse. Georg Thieme Verlag Stuttgart - New York.
Dichlorobis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato)zirco- nium(IV), [Zr(BH4)2Cl2(dabco)2](ZrBDC), as a new, stable, and versatile bench top reducing agent: Reduction of imines and enamines, reductive amination of aldehydes and ketones and reductive methylation of amines
Firouzabadi, Habib,Iranpoor, Nasser,Alinezhad, Heshmatollah
, p. 143 - 151 (2007/10/03)
The reducing agent is easily prepared in an almost quantitative yield from commercially available starting materials. This compound is stable under mild aqueous acidic conditions (pH 4-6) and survives in H2O for several days without losing its reducing abilities. ZrBDC has been successfully used for the reduction of imines and enamines, reductive amination of aldehydes and ketones, and reductive methylation of amines.
Addition of NN-Dimethylaniline Oxides to Nitrilium Salts and to Dimethyl Acetylenedicarboxylate. Direct Alkylamination of NN-Dimethylanilines
Sheradsky, Tuvia,Nov, Eliahu
, p. 527 - 530 (2007/10/02)
NN-Dimethylaniline oxide (1) and its ring-substituted derivatives react with N-alkylacetonitrilium salts to give the corresponding 2- and 4-(N-alkylacetamido)dimethylanilines.The mechanism, Which involves migration of an amide group from the aniline nitrogen onto the ring, is discussed.Addition of the oxide (1) to dimethyl acetylenedicarboxylate leads either to demethylation of the aniline (main path in dichloromethane) or to a rearrengement, which involves migration of the succinyl moiety onto the ortho-carbon (in ethanol).
