Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Jones-Mensah, Ebenezer; Karki, Megha; Magolan, Jakob

doi:10.1055/s-0035-1560429

Cited by 136 publications

(27 citation statements)

References 69 publications

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“…The following chapters aim to provide an overview of recent developments in oxidative functionalization based on the use of a sulfoxide as either the reactant or the oxidant. The use of the simplest sulfoxide, DMSO, as a synthon and reagent in organic chemistry has been previously expertly reviewed by the groups of Magolan 145 and Wu, 146 and these works should be sought out for additional detail on historic transformations and developments preceding the scope of this review.…”

Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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“…Degradation product A3 (4) can be expected in higher concentrations, Venetoclax can react with the methyl(methylene)sulfonium species, after which a second Pummerer-type reaction and a subsequent reaction with another venetoclax molecule would result in the dimer (4) (Scheme 3). Alternatively, venetoclax could dimerize through a reaction with formaldehyde (Scheme 4) [38][39][40]. A similar, solvent free reaction with formaldehyde was observed with an addition of a Lewis base, calcium oxide [41].…”

Section: Degradation Pathways Of Venetoclaxmentioning

confidence: 81%

“…Another degradation product, formed in acidic and basic conditions was degradation product A3/B3 (4). It is a dimer, connecting two venetoclax molecules through a methylene bridge, the origin of which is probably DMSO used in the solvent [38,39]. DMSO can undergo a Pummerer-type reaction, resulting in a methyl(methylene)sulfonium species.…”

Section: Degradation Pathways Of Venetoclaxmentioning

confidence: 99%

“…DMSO can undergo a Pummerer-type reaction, resulting in a methyl(methylene)sulfonium species. The hydrolysis of methyl(methylene)sulfonium species would result in formaldehyde formation (Scheme 2) [38]. Venetoclax can react with the methyl(methylene)sulfonium species, after which a second Pummerer-type reaction and a subsequent reaction with another venetoclax molecule would result in the dimer (4) (Scheme 3).…”

Section: Degradation Pathways Of Venetoclaxmentioning

confidence: 99%

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On the Stability and Degradation Pathways of Venetoclax under Stress Conditions

Žigart

Črnugelj²,

Ilaš

et al. 2020

Pharmaceutics

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Venetoclax is an orally bioavailable, B-cell lymphoma-2 (BCL-2) selective inhibitor, used for the treatment of various types of blood cancers, such as chronic lymphocytic leukemia (CLL) and small lymphocytic lymphoma (SLL). In this study we investigated the degradation of venetoclax under various stress conditions including acidic, basic, oxidative, photolytic and thermolytic conditions. We isolated and identified six of its main degradation products produced in forced degradation studies. The structures of the isolated degradation products were determined by using nuclear magnetic resonance (NMR) spectroscopy, high resolution mass spectrometry (HRMS) and infrared (IR) spectroscopy. Additionally, one oxidation degradation product was identified with comparison to a commercially obtained venetoclax impurity. We proposed the key degradation pathways of venetoclax in solution. To the best of our knowledge, no structures of degradation products of venetoclax have been previously published. The study provides novel and primary knowledge of the stability characteristics of venetoclax under stress conditions. Venetoclax is currently the only BCL-2 protein inhibitor on the market. In addition to single agent treatment, it is effective in combinational therapy, so future drug development involving venetoclax can be expected. A better insight into the stability properties of the therapeutic can facilitate future studies involving venetoclax and aid in the search of new similar therapeutics.

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“…[25] The second side-product arises from the C-3 formylation of the 2-phenylimidazo[1,2-a]pyridine using DMSO as the carbon source of the formyl moiety. [26] In addition, the stability of the sulfone 3 was also studied. After 24 h under green light irradiation in DMSO, 82 % of 3 were recovered and only 60 % when the sulfone 3 was placed under our reaction conditions.…”

mentioning

confidence: 99%

Three‐Component C–H Bond Sulfonylation of Imidazoheterocycles by Visible‐Light Organophotoredox Catalysis

et al. 2020

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The first entirely visible‐light photoredox catalyzed sulfonylation of imidazoheterocycles has been developed. This transformation demonstrates an efficient C–H functionalization for the straightforward synthesis of novel C‐3 sulfonylated imidazoheterocycles from various imidazopyridines and diaryliodonium salts with different electronic and steric properties and easy to handle DABCO‐bis(sulfur dioxide). The reaction proceeds in moderate to good yields under mild conditions at room temperature using the inexpensive organophotocatalyst EosinY·Na2 and shows a high functional group tolerance (37 examples).

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Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Cited by 136 publications

References 69 publications

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

On the Stability and Degradation Pathways of Venetoclax under Stress Conditions

Three‐Component C–H Bond Sulfonylation of Imidazoheterocycles by Visible‐Light Organophotoredox Catalysis

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