Gold(III) N-Heterocyclic Carbene Complexes Mediated Synthesis of β-Enaminones From 1,3-Dicarbonyl Compounds and Aliphatic Amines

2011 ◽  
Vol 50 (5) ◽  
pp. 1840-1848 ◽  
Author(s):  
Manoja K. Samantaray ◽  
Chandrakanta Dash ◽  
Mobin M. Shaikh ◽  
Keliang Pang ◽  
Ray J. Butcher ◽  
...  
Keyword(s):  
Aliphatic Amines ◽  
Dicarbonyl Compounds ◽  
Carbene Complexes

Dinuclear cobalt complexes supported by biphenol and binaphthol-derived bis(salicylaldimine) ligands: synthesis, characterization and catalytic application in β-enaminone synthesis from 1,3-dicarbonyl compounds and aliphatic amines

2020 ◽  
Vol 44 (35) ◽  
pp. 15109-15121
Author(s):  
Adelew Estifanos Filkale ◽  
Chandni Pathak
Keyword(s):  
Cobalt Complexes ◽  
Aliphatic Amines ◽  
Ambient Conditions ◽  
Dicarbonyl Compounds ◽  
Catalytic Application ◽  
Scaffolding Ligands

Biaryl scaffolding ligands form dicobalt clusters, which serve as efficient catalysts in enaminone synthesis under ambient conditions.

ChemInform Abstract: Metal-Free Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds via Oxidative C-C Bond Cleavage of Tertiary Aliphatic Amines.

ChemInform ◽  
2015 ◽  
Vol 46 (5) ◽  
pp. no-no
Author(s):  
Li-Juan Xing ◽  
Xi-Mei Wang ◽  
Hong-Ying Li ◽  
Wen Zhou ◽  
Ning Kang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Aliphatic Amines ◽  
Dicarbonyl Compounds ◽  
Metal Free

Metal-free synthesis of methylene-bridged bis-1,3-dicarbonyl compounds via oxidative C–C bond cleavage of tertiary aliphatic amines

RSC Advances ◽  
2014 ◽  
Vol 4 (51) ◽  
pp. 26783-26786 ◽  
Author(s):  
Li-Juan Xing ◽  
Xi-Mei Wang ◽  
Hong-Ying Li ◽  
Wen Zhou ◽  
Ning Kang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Aliphatic Amines ◽  
Dicarbonyl Compounds ◽  
Oxidative Reaction ◽  
Metal Free

A metal-free Bu4NI mediated oxidative reaction utilizing tertiary aliphatic amines and 1,3-dicarbonyl compounds for the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds has been developed. This reaction involved an unexpected C–C bond cleavage of tertiary aliphatic amines.

Uncatalyzed Synthesis of β-Enamino Ketones in PEG - Water

2008 ◽  
Vol 61 (7) ◽  
pp. 552 ◽  
Author(s):  
Babasaheb P. Bandgar ◽  
Sachin A. Patil ◽  
Balaji L. Korbad ◽  
Sunita B. Bandgar ◽  
Baliram S. Hote
Keyword(s):  
Polyethylene Glycol ◽  
Aliphatic Amines ◽  
Dicarbonyl Compounds ◽  
Enamino Ketones ◽  
Excellent Yield ◽  
Peg 600

β-Enamino ketones have been synthesized in excellent yield by the reaction of aromatic or aliphatic amines with 1,3-dicarbonyl compounds in polyethylene glycol (PEG)-600–water. The PEG-600 is recycled and reused.

Efficient and Versatile Catalytic Systems for the N-Methylation of Primary Amines with Methanol Catalyzed by N-Heterocyclic Carbene Complexes of Iridium

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4617-4626 ◽  
Author(s):  
Ken-ichi Fujita ◽  
Genki Toyooka ◽  
Akiko Tuji
Keyword(s):  
Low Temperatures ◽  
Aromatic Amines ◽  
Catalytic Performance ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Iridium Complexes ◽  
Reaction Conditions ◽  
Catalytic Systems ◽  
Carbene Complexes ◽  
Amine Compounds

Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an N-heterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50–90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.

Mechanochemical changes on cyclometalated Ir(iii) acyclic carbene complexes – design and tuning of luminescent mechanochromic transition metal complexes

2020 ◽  
Vol 7 (3) ◽  
pp. 786-794 ◽  
Author(s):  
Jingqi Han ◽  
Kin-Man Tang ◽  
Shun-Cheung Cheng ◽  
Chi-On Ng ◽  
Yuen-Kiu Chun ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Carbene Complexes ◽  
New Class

A new class of luminescent cyclometalated Ir(iii) complexes with readily tunable mechanochromic properties derived from the mechanically induced trans-to-cis isomerization have been developed.

Dicarbonyl derived post-translational modifications: chemistry bridging biology and aging-related disease

2020 ◽  
Vol 64 (1) ◽  
pp. 97-110
Author(s):  
Christian Sibbersen ◽  
Mogens Johannsen
Keyword(s):  
Mass Spectrometry ◽  
Future Research ◽  
Amino Acid Residues ◽  
Post Translational Modification ◽  
Dicarbonyl Compounds ◽  
Protein Targets ◽  
Post Translational Modifications ◽  
Reactive Protein ◽  
Glycation End Products ◽  
Direct Mass Spectrometry

Abstract In living systems, nucleophilic amino acid residues are prone to non-enzymatic post-translational modification by electrophiles. α-Dicarbonyl compounds are a special type of electrophiles that can react irreversibly with lysine, arginine, and cysteine residues via complex mechanisms to form post-translational modifications known as advanced glycation end-products (AGEs). Glyoxal, methylglyoxal, and 3-deoxyglucosone are the major endogenous dicarbonyls, with methylglyoxal being the most well-studied. There are several routes that lead to the formation of dicarbonyl compounds, most originating from glucose and glucose metabolism, such as the non-enzymatic decomposition of glycolytic intermediates and fructosyl amines. Although dicarbonyls are removed continuously mainly via the glyoxalase system, several conditions lead to an increase in dicarbonyl concentration and thereby AGE formation. AGEs have been implicated in diabetes and aging-related diseases, and for this reason the elucidation of their structure as well as protein targets is of great interest. Though the dicarbonyls and reactive protein side chains are of relatively simple nature, the structures of the adducts as well as their mechanism of formation are not that trivial. Furthermore, detection of sites of modification can be demanding and current best practices rely on either direct mass spectrometry or various methods of enrichment based on antibodies or click chemistry followed by mass spectrometry. Future research into the structure of these adducts and protein targets of dicarbonyl compounds may improve the understanding of how the mechanisms of diabetes and aging-related physiological damage occur.

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