ChemInform Abstract: Oxidative Cyclization of Dialdehydes with Alcohols and 1,3-Dicarbonyl Compounds under Rh(III)/Cu(II) Conditions.

ChemInform ◽  
2016 ◽  
Vol 47 (12) ◽  
pp. no-no
Author(s):  
Takanori Matsuda ◽  
Kentaro Suzuki ◽  
Shinya Abe ◽  
Haruki Kirikae ◽  
Noboru Okada
Keyword(s):  
Oxidative Cyclization ◽  
Dicarbonyl Compounds

A Highly Efficient Heterogeneous Copper-Catalyzed Oxidative Cyclization of Benzylamines and 1,3-Dicarbonyl Compounds To Give Trisubstituted Oxazoles

Synthesis ◽  
2019 ◽  
Vol 51 (16) ◽  
pp. 3091-3100
Author(s):  
Li Wei ◽  
Shengyong You ◽  
Yuxin Tuo ◽  
Mingzhong Cai
Keyword(s):  
Copper Catalyst ◽  
Oxidative Cyclization ◽  
Dicarbonyl Compounds ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Intermolecular Cyclization ◽  
Step Procedure ◽  
Mcm 41

The heterogeneous copper-catalyzed cascade oxidative cyclization between benzylamines and 1,3-dicarbonyl compounds was achieved by using the 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst and t-BuOOH (TBHP) as oxidant, with iodine as additive, under mild conditions, yielding a wide variety of 2,4,5-trisubstituted oxazoles in mostly good to excellent yields. This heterogeneous copper catalyst can be facilely prepared via a simple two-step procedure from readily available and inexpensive reagents and exhibits a slightly higher activity than Cu(OAc)2. MCM-41-2N-Cu(OAc)2 is also easy to recover and can be recycled up to eight times with almost consistent activity. The reaction is the first example of heterogeneous copper-catalyzed intermolecular cyclization for the construction of polysubstituted oxazoles.

Hypoiodite-catalysed oxidative cyclisation of Michael adducts of chalcones with 1,3-dicarbonyl compounds: a facile and versatile approach to substituted furans and cyclopropanes

2016 ◽  
Vol 52 (89) ◽  
pp. 13097-13100 ◽  
Author(s):  
Wen-Chao Gao ◽  
Fei Hu ◽  
Jun Tian ◽  
Xing Li ◽  
Wen-Long Wei ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
Dicarbonyl Compounds ◽  
Michael Adducts ◽  
Oxidative Cyclisation ◽  
Substituted Furans

Hypoiodite catalysis for selective oxidative cyclization has been developed, yielding either furans or cyclopropanes with excellent diastereoselectivity.

Oxidative cyclization of dialdehydes with alcohols and 1,3-dicarbonyl compounds under Rh(III)/Cu(II) conditions

Tetrahedron ◽  
2015 ◽  
Vol 71 (49) ◽  
pp. 9264-9270 ◽  
Author(s):  
Takanori Matsuda ◽  
Kentaro Suzuki ◽  
Shinya Abe ◽  
Haruki Kirikae ◽  
Noboru Okada
Keyword(s):  
Oxidative Cyclization ◽  
Dicarbonyl Compounds

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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