Regioselective [3 + 2]-annulation of hydrazonyl chlorides with 1,3-dicarbonyl compounds for assembling of polysubstituted pyrazoles

2018 ◽  
Vol 16 (42) ◽  
pp. 7811-7814 ◽  
Author(s):  
Kun Liu ◽  
Xinye Shang ◽  
Yuyu Cheng ◽  
Xiaoyong Chang ◽  
Pengfei Li ◽  
...  
Keyword(s):  
Dicarbonyl Compounds ◽  
Hydrazonyl Chlorides

The facile approach to polysubstituted pyrazoles from hydrazonyl chlorides and 1,3-dicarbonyl compounds has been developed. Hydrazonyl chlorides reacted with N-phenyl-3-oxobutanamides smoothly to afford a series of polysubstituted pyrazoles in 67–98% yields via the [3 + 2]-cycloaddition.

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.

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...

Rh(III)-Catalyzed Cascade Nucleophilic Addition/Annulation of 2-Diazo-1,3-diketones with 1,3-Dicarbonyl Compounds To Access 6,7-Dihydrobenzofuran-4(5H)-ones

2021 ◽  
Author(s):  
Yinsong Wu ◽  
Xinwei He ◽  
Mengqing Xie ◽  
Ruxue Li ◽  
Yi Ning ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Dicarbonyl Compounds

Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)-para-Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds

2021 ◽  
Author(s):  
Zong-Wang Qiu ◽  
Xue-Tao Xu ◽  
Han-Peng Pan ◽  
Zhen-Sheng Jia ◽  
Ai-Jun Ma ◽  
...  
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Dicarbonyl Compounds ◽  
Brönsted Acid ◽  
Acid Catalyzed

ChemInform Abstract: Transformations of β-Dicarbonyl Compounds by Reactions of Their Transition Metal Complexes with Carbon and Oxygen Electrophiles

ChemInform ◽  
2010 ◽  
Vol 27 (27) ◽  
pp. no-no
Author(s):  
M. MORENO-MANAS ◽  
J. MARQUET ◽  
A. VALLRIBERA
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Dicarbonyl Compounds

ChemInform Abstract: CONDENSATION OF 4-AMINO-3-HYDRAZINO-1,2,4-TRIAZOLINE-5-THIONE WITH α- AND β-DICARBONYL COMPOUNDS

1978 ◽  
Vol 9 (36) ◽  
Author(s):  
A. D. SINEGIBSKAYA ◽  
K. I. PASHKEVICH ◽  
V. I. SALOUTIN ◽  
N. A. KLYUEV ◽  
E. KH. DANK
Keyword(s):  
Dicarbonyl Compounds

scholarly journals Mizoroki–Heck type reactions and synthesis of 1,4-dicarbonyl compounds by heterogeneous organic semiconductor photocatalysis

2021 ◽  
Vol 23 (5) ◽  
pp. 2017-2024
Author(s):  
Jagadish Khamrai ◽  
Saikat Das ◽  
Aleksandr Savateev ◽  
Markus Antonietti ◽  
Burkhard König
Keyword(s):  
Visible Light ◽  
Vinyl Acetate ◽  
Organic Semiconductor ◽  
Alkyl Halides ◽  
Visible Light Photocatalysis ◽  
Dicarbonyl Compounds ◽  
Semiconductor Photocatalysis ◽  
Type Coupling ◽  
Styrene Derivatives ◽  
Tertiary Alkyl

We report the synthesis of 1,4-dicarbonyl compounds and substituted alkenes (Mizoroki–Heck type coupling) starting from secondary and tertiary alkyl halides and vinyl acetate or styrene derivatives using visible-light photocatalysis.

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