Diazocarbonyl and Related Compounds in the Synthesis of Azoles

Budeev, Anton; Kantin, Grigory; Dar’in, Dmitry; Krasavin, Mikhail

doi:10.3390/molecules26092530

Cited by 27 publications

(4 citation statements)

References 230 publications

(229 reference statements)

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“…74 The reactions of α-diazocarbonyls through ketenes and metal-carbenoids offer entry to a wide range of biologically important heterocyclic motifs. [75][76][77][78] α-Diazocarbonyl compounds are easily prepared in laboratory by different methods such as i) Regitz diazo-transfer reaction, ii) Earnst-Eistert method, and iii) by oxidation of hydrazones. [79][80][81] Singh and coworkers at the University of Botswana have been investigating the reaction of 2-diazoketones and ethyl diazoacetate through ketenes and carbenoids with the objective to discover new and convenient routes for the synthesis of heterocyclic compounds.…”

Section: Scheme 11mentioning

confidence: 99%

An account of organic chemistry research in Botswana

Singh¹,

Majinda²,

Masesane³

2022

Arkivoc

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The present paper gives an account of research in different areas of organic chemistry carried out at the University of Botswana. It describes the results of phytochemical investigations carried out on eight species of genus Erythrina. Several new alkaloids and non-alkaloids have been isolated and screened for different biological activities. Physicochemical properties and fatty acids composition of some oils are described as well. The paper also documents some synthetic approaches to natural products and their derivatives, β-amino acids, β-lactams, 1,3,4-oxadiazolines, spirooxindole-2-azetidinones and spirooxindole-oxiranes. The synthetic approaches include the elaboration of the Diels-Alder product of furan and some dienophiles to give the natural product oryzoxymycin and cyclohexyl-β-amino acids. In addition, studies on synthesis of chromane/chromene ring systems are summarized. The application of α-diazoketones and ethyl diazoacetate in the synthesis of βlactams, 1,3,4-oxadiazoline, spirooxindole-2-azetidinones, and spirooxindole-oxiranes is described. Some oxidative, reductive, and other reactions of β-lactams are discussed. In the green chemistry domain, results on grinding-induced synthesis of benzoxazines and microwave-assisted synthesis of benzil diimines are presented. Bis(acetylacetonato)copper(II)-catalyzed oxidation reactions of hydrazones and the sec-alcoholic group of benzoins to azines and 1,2-diketones, respectively, are described. In addition, the PdCl2-catalyzed transfer hydrogenation of alkenes to alkanes in the presence Zn powder is accounted.

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Section: Scheme 11mentioning

confidence: 99%

An account of organic chemistry research in Botswana

Singh¹,

Majinda²,

Masesane³

2022

Arkivoc

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“…The plethora of known diazocarbonyl and related compounds, 25 several of them commercially available, present an opportunity to expand the search for suitable organotitanium complexes with pendant functionality, for consideration as antitumor agents in a spectrum of targeted therapeutic applications. The possibility of engaging any of the three types of organotitanium complexes mentioned above, along with an expanded choice of small molecules, for insertion reactions into the active Ti-C σ-bond, aiming at controlling the stability and aqueous solubility of the antitumor candidates, gives rise to a great number of possible effective cytotoxic complexes.…”

Section: Fine Chemical Engineering Volume 3 Issue 2|2022| 173mentioning

confidence: 99%

New Antitumor Organotitanium Complexes with a Pendant Biologically Active Diazo Group

Arzoumanidis

2022

Fine Chemical Engineering

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The ligand of antitumor organotitanium or other metallodrug complexes plays a pivotal role in determining the mechanism of their cytotoxic action. Although the specific contribution of several ligands is generally well established, our understanding of the overall mechanism of the cytotoxic action of the complexes themselves is limited and incomplete in most cases, except perhaps in the case of cis-platin. A strategy to monitor the mode of cytotoxic action of candidate antitumor complexes requires tagging with bioactive side chains like a diazo group, for in-cell site-specific labelling. In this review we discuss new methods for the preparation of potential antitumor organotitanium complexes with a pendant diazo group, aiming at better understanding their mode of cytotoxic action. By introducing this new class of titanium-based potential antitumor agents, we hope to contribute to the world-wide effort in this important area of medicinal chemistry research, for an ultimate usable titanium-based antitumor drug. The following figure represents a model reaction depicting the methodology, for the formation of a bioactive Titanium complex with a pendant diazo group. Moreover, in this case, a scheme is required that represents all the possibilities of formation of the bioactive complex of titanium with a pendant diazo group.

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“…In organic synthesis, diazo compounds have been relevant ever since their discovery because of their high reactivity. [56][57][58][59][60][61][62][63] Several transition metals such as Rh, Cu, Ru, Co and Fe find extensive use in decomposing diazo compounds to yield the corresponding metal carbenes with characteristics that are imperative to bring about important organic transformations such as XÀ H (X=C, O, N, S, etc.) insertion, cross coupling, cyclopropanation, cycloaddition and rearrangement.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of Sulfonic Acid to Sulfonic Ester Using Diazo Compound under Mild Reaction Conditions in the Absence of Additives

2022

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Sulfonate esters are important owing to their special bioactivities. Nevertheless, severe reaction conditions, use of expensive catalysts along with additives and the numerous side reactions in the previously reported methods demand the development of valid approaches for the synthesis of aryl sulfonate esters. Herein, we report a facile synthetic strategy utilizing the V IV based catalyst for the carbene insertion into the OÀ H bond of sulfonic acids to afford sulfonate esters up to 90 % yield under mild reaction conditions. All the synthesized sulfonate esters were fully characterized by using standard spectroscopic and analytical techniques such as NMR, IR, ESI-MS and single crystal XRD analysis.

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Diazocarbonyl and Related Compounds in the Synthesis of Azoles

Cited by 27 publications

References 230 publications

An account of organic chemistry research in Botswana

An account of organic chemistry research in Botswana

New Antitumor Organotitanium Complexes with a Pendant Biologically Active Diazo Group

Functionalization of Sulfonic Acid to Sulfonic Ester Using Diazo Compound under Mild Reaction Conditions in the Absence of Additives

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