Manganese-Catalyzed Benzene Synthesis by [2+2+2] Coupling of 1,3-Dicarbonyl Compound and Terminal Acetylene

2008 ◽  
Vol 130 (25) ◽  
pp. 7792-7793 ◽  
Author(s):  
Hayato Tsuji ◽  
Ken-ichi Yamagata ◽  
Taisuke Fujimoto ◽  
Eiichi Nakamura
Keyword(s):  
Terminal Acetylene ◽  
Dicarbonyl Compound

ChemInform Abstract: Manganese-Catalyzed Benzene Synthesis by [2 + 2 + 2] Coupling of 1,3-Dicarbonyl Compound and Terminal Acetylene.

ChemInform ◽  
2008 ◽  
Vol 39 (44) ◽  
Author(s):  
Hayato Tsuji ◽  
Ken-ichi Yamagata ◽  
Taisuke Fujimoto ◽  
Eiichi Nakamura
Keyword(s):  
Terminal Acetylene ◽  
Dicarbonyl Compound

Role of Methylglyoxal in Diabetic Cardiovascular and Kidney Diseases: Insights from Basic Science for Application into Clinical Practice

2018 ◽  
Vol 24 (26) ◽  
pp. 3072-3083 ◽  
Author(s):  
Sowndramalingam Sankaralingam ◽  
Angham Ibrahim ◽  
MD Mizanur Rahman ◽  
Ali H. Eid ◽  
Shankar Munusamy
Keyword(s):  
Therapeutic Strategy ◽  
Kidney Diseases ◽  
Vascular Dysfunction ◽  
Dicarbonyl Compound ◽  
Renal Complications ◽  
Lysine Residues ◽  
Patients With Diabetes ◽  
Prevalence Of Diabetes Mellitus

Background: The incidence and prevalence of diabetes mellitus are increasing globally at alarming rates. Cardiovascular and renal complications are the major cause of morbidity and mortality in patients with diabetes. Methylglyoxal (MG) - a highly reactive dicarbonyl compound – is increased in patients with diabetes and has been implicated to play a detrimental role in the etiology of cardiovascular and renal complications. Derived from glucose, MG binds to arginine and lysine residues in proteins, and the resultant end products serve as surrogate markers of MG generation in vivo. Under normal conditions, MG is detoxified by the enzyme glyoxalase 1 (Glo1), using reduced glutathione as a co-factor. Elevated levels of MG is known to cause endothelial and vascular dysfunction, oxidative stress and atherosclerosis; all of which are risk factors for cardiovascular diseases. Moreover, MG has also been shown to cause pathologic structural alterations and impair kidney function. Conversely, MG scavengers (such as N-acetylcysteine, aminoguanidine or metformin) or Nrf2/Glo1 activators (such as trans-resveratrol / hesperetin) are shown to be useful in preventing MG-induced cardiovascular and renal complications in diabetes. However, clinical evidence supporting the MG lowering properties of these agents are limited and hence, need further investigation. Conclusion: Reducing MG levels directly using scavengers or indirectly via activation of Nrf2/Glo1 may serve as a novel and potent therapeutic strategy to counter the deleterious effects of MG in diabetic complications.

2-Deoxyglucosone: A New C6-α-Dicarbonyl Compound in the Maillard Reaction of d-Fructose with γ-Aminobutyric Acid

2018 ◽  
Vol 66 (44) ◽  
pp. 11806-11811 ◽  
Author(s):  
Philipp Bruhns ◽  
Martin Kaufmann ◽  
Timo Koch ◽  
Lothar W. Kroh
Keyword(s):  
Maillard Reaction ◽  
Aminobutyric Acid ◽  
Dicarbonyl Compound

Irreversible inhibition of aldolase by a phosphorylated α-dicarbonyl compound

2008 ◽  
Vol 23 (1) ◽  
pp. 21-27 ◽  
Author(s):  
Nicolas Chabot ◽  
Virginie Vinatier ◽  
Thierry Gefflaut ◽  
Cecile Baudoin ◽  
Frederic Rodriguez ◽  
...  
Keyword(s):  
Dicarbonyl Compound ◽  
Irreversible Inhibition

N-Iodosuccinimide-Initiated Spirocyclopropanation of Styrenes with 1,3-Dicarbonyl Compound for the Synthesis of Spirocyclopropanes

2016 ◽  
Vol 81 (15) ◽  
pp. 6546-6553 ◽  
Author(s):  
Ping Qian ◽  
Bingnan Du ◽  
Ruichun Song ◽  
Xiaodong Wu ◽  
Haibo Mei ◽  
...  
Keyword(s):  
Dicarbonyl Compound

scholarly journals Effect of Reactivity on Kinetics and a Mechanistic Investigation of the Reaction between Dimethyl Acetylenedicarboxylate and 1,3-Dicarbonyl Compounds in the Presence of a Catalyst: A Spectrophotometric Approach

2018 ◽  
Vol 43 (1) ◽  
pp. 79-90 ◽  
Author(s):  
Mahdieh Darijani ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Mehdi Shahraki
Keyword(s):  
Structural Effect ◽  
Similar Reaction ◽  
Dimethyl Acetylenedicarboxylate ◽  
Dicarbonyl Compounds ◽  
Dicarbonyl Compound ◽  
Rate Determining Step ◽  
Mechanistic Investigation ◽  
Differential Behaviour ◽  
Fourth Step ◽  
Step Step

A kinetic and mechanistic investigation, using conventional UV-Vis spectrophotometry, of the reaction between dimethyl acetylenedicarboxylate (DMAD) and 1,3-dicarbonyl compounds including acetylacetone (ACAC) and dibenzoylmethane (DBM), has been conducted in a methanol environment with triphenylarsine (TPA) acting as a catalyst. Previously, in a similar reaction, triphenylphosphine (TPP) (instead of TPA) had been employed as a reactant (not a catalyst) for the generation of an ylide (final product). In the present work, of significance is the differential behaviour of TPA which, as a catalyst in the reaction environment, leads to a cyclopropane compound. Of other significance is the different behaviours of the two reactants in the kinetics and mechanism of the reaction. In previous work, TPP acted as a weak nucleophile (a reactant), so the first step of the reaction was recognised as the rate-determining step (RDS). Here, TPA reacts as a stronger nucleophile and a catalyst, resulting in the fourth step of the reaction (step4, k4, a proton transfer process) being recognised as the RDS. The reaction followed second-order kinetics. The proposed mechanism was adapted in accord with the experimental results and the steady-state assumption. The results showed that the reaction rate decreases in the presence of DBM, which participates in the second step (step2), compared to ACAC when it is present as another 1,3-dicarbonyl compound (structural effect). In addition, in previous work, the partial order of the reaction with respect to the 1,3-dicarbonyl compound was zero, while it is one in the present work. As a significant result, not only did a change in the structure of one of the reactants (TPA instead of TPP) create a different product, but also the kinetics and reaction mechanism changed. In addition, the reaction is enthalpy-controlled.

scholarly journals Domino reactions in the synthesis of heterocyclic natural products and analogs

2004 ◽  
Vol 76 (11) ◽  
pp. 1967-1983 ◽  
Author(s):  
L. F. Tietze ◽  
N. Rackelmann
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Domino Reactions ◽  
Complex Molecules ◽  
Enol Ethers ◽  
Dicarbonyl Compound ◽  
Bond Forming ◽  
Enantioselective Total Synthesis ◽  
Subsequent Transformation ◽  
Diels Alder Reaction

Domino reactions are defined as processes of two or more bond-forming reactions under identical conditions, in which the subsequent transformation takes place at the functionalities obtained in the former transformation. They allow the efficient synthesis of complex molecules from simple substrates in an ecologically and economically favorable way. A very powerful domino process is the domino Knoevenagel–hetero-Diels–Alder reaction, in which an aldehyde or an beta-ketoester is condensed with a 1,3-dicarbonyl compound or a heteroanalog to give a 1-oxa-1,3-butadiene, which can undergo an inter- or intramolecular hetero-Diels–Alder reaction with dienophiles such as enol ethers or alkenes. The products are dihydropyrans, which can be transformed in a variety of ways. Thus, an extension of the process is the synthesis of highly substituted pyrrolidines, piperidines, and azepanes using aminoaldehydes. The process has also been employed for the enantioselective total synthesis of a variety of alkaloids, such as indol- and ipecacuanha alkaloids. In another domino process, erythrina and homoerythrina alkaloids have been prepared from simple phenylethylamines and ketoesters.

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