Organoselenium chemistry. Conversion of cyclic ketones and .beta.-dicarbonyl compounds to enones

1974 ◽  
Vol 39 (14) ◽  
pp. 2133-2135 ◽  
Author(s):  
Hans J. Reich ◽  
James M. Renga ◽  
Ieva L. Reich
Keyword(s):  
Cyclic Ketones ◽  
Dicarbonyl Compounds

A Green Approach for Efficient α-Halogenation of β-Dicarbonyl Compounds and Cyclic Ketones Using N-Halosuccinimides in Ionic Liquids.

ChemInform ◽  
2006 ◽  
Vol 37 (19) ◽  
Author(s):  
H. M. Meshram ◽  
P. N. Reddy ◽  
P. Vishnu ◽  
K. Sadashiv ◽  
J. S. Yadav
Keyword(s):  
Ionic Liquids ◽  
Cyclic Ketones ◽  
Dicarbonyl Compounds ◽  
Green Approach

A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids

2006 ◽  
Vol 47 (6) ◽  
pp. 991-995 ◽  
Author(s):  
H.M. Meshram ◽  
P.N. Reddy ◽  
P. Vishnu ◽  
K. Sadashiv ◽  
J.S. Yadav
Keyword(s):  
Ionic Liquids ◽  
Cyclic Ketones ◽  
Dicarbonyl Compounds ◽  
Green Approach

Metal and Boron Derivatives of Fluorinated Cyclic 1,3-Dicarbonyl Compounds

2009 ◽  
Vol 64 (5) ◽  
pp. 541-550 ◽  
Author(s):  
Dmitri V. Sevenard ◽  
Oleg G. Khomutov ◽  
Nadezhda S. Boltachova ◽  
Vera I. Filyakova ◽  
Vera Vogel ◽  
...  
Keyword(s):  
X Ray Diffraction ◽  
Cyclic Ketones ◽  
Chelate Complexes ◽  
Dicarbonyl Compounds ◽  
X Ray ◽  
Derivatives Of ◽  
Boron Chelate

Starting from the corresponding cyclic 1,3-diketones or other precursors (cyclic ketones as well as lactones), several new salts and chelate complexes of fluorinated 1,3-dicarbonyls were obtained. Their preparative significance was demonstrated by straightforward syntheses of fluorinated pyrazoles, benzimidazoles and 1,7-ketoesters. The structure of a boron chelate of 2-(trifluoroacetyl)- cyclohexanone was investigated by X-ray diffraction.

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.

l-Prolinal Dithioacetal: A Highly Effective Organocatalyst for the Direct Nitro-Michael Addition to Selected Cyclic and Aromatic Ketones

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3356-3368
Author(s):  
Piotr Pomarański ◽  
Zbigniew Czarnocki
Keyword(s):  
Michael Addition ◽  
Ring Size ◽  
Cyclic Ketones ◽  
Asymmetric Syntheses ◽  
Aromatic Ketones ◽  
Ring Systems ◽  
Effective Catalyst ◽  
Acetophenone Derivatives ◽  
Highly Effective ◽  
Related Compounds

The synthesis of novel l-prolinal dithioacetal and its application as an organocatalyst for the direct Michael addition of cyclic ketones and acetophenone derivatives to trans-β-nitrostyrene and related compounds is described. The prolinal dithioacetal acts as effective catalyst in the case of cyclic ketones of different ring size, in particular five- and six-membered examples, as well as larger and smaller ring systems. High enantioselectivity and diastereoselectivity is observed for different substrates and trans-β-nitrostyrenes. Also, the first asymmetric syntheses of selected 2-methyl-4-nitro-1,3-diphenylbutan-1-one derivatives by application of the obtained organocatalyst is presented.

ChemInform Abstract: CONDENSATION OF O-AMINOPHENOL AND α-DICARBONYL COMPOUNDS. PART 1. BENZOXAZINES

1978 ◽  
Vol 9 (18) ◽  
Author(s):  
E. BELGODERE ◽  
R. BOSSIO ◽  
V. PARRINI ◽  
R. PEPINO
Keyword(s):  
Dicarbonyl Compounds

scholarly journals Stereoselective Tandem Iridium-Catalyzed Alkene Isomerization-Cope Rearrangement of ω-diene Epoxides: Efficient Access to Acyclic 1,6-Dicarbonyl Compounds

2021 ◽  
Author(s):  
Rahul Suresh ◽  
Itai Massad ◽  
Ilan Marek
Keyword(s):  
Bond Cleavage ◽  
Cope Rearrangement ◽  
Dicarbonyl Compounds ◽  
Alkene Isomerization ◽  
Efficient Access

The Cope rearrangement of 2,3-divinyloxiranes, a rare example of epoxide C-C bond cleavage, results in 4,5-dihydrooxepines which are amenable to hydrolysis, furnishing 1,6-dicarbonyl compounds containing two contiguous stereocenters at the 3- and 4- positions. We employ...

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