Recent Developments in the Synthesis and Application of Sultones

Mondal, Shovan

doi:10.1021/cr2003294

Cited by 77 publications

(51 citation statements)

References 126 publications

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“…Since no catalysts and cheap reagents were used, this practical approach might be preferred as a relatively "green process". The new synthetic method expands the scope of methods currently available to introduce the sultone functional group [8]. Meanwhile, this methodology could find applications in the synthesis of naturally occurring sultones.…”

Section: Synthesis Of S-camentioning

confidence: 99%

“…Methods used to synthesize sultones and include intramolecular Diels-Alder reactions, ring-closing metathesis, Pd-catalyzed intramolecular coupling reactions, Rh-catalyzed C-H insertion, Rh-catalyzed carbene cyclization cycloaddition cascade reactions, nucleophilic addition reactions etc. [7,8]. The major step in synthesis of sultone is ring-closing reaction which was often complicated by the need to use special and expensive catalysts such as Rh and Pd [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

“…[7,8]. The major step in synthesis of sultone is ring-closing reaction which was often complicated by the need to use special and expensive catalysts such as Rh and Pd [8][9][10]. However, the search for a simple and short synthesis of sultones has never been suspended for a moment in recent years [11].…”

Section: Introductionmentioning

confidence: 99%

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New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

Yan

Zhang

et al. 2015

Molecules

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There has been no remarkable progress in the synthesis of sultones in recent years. To facilitate more detailed studies of this functional group, we found a new method to synthesize the sulfonic acid lactone derivatives and finish its ring-closing reaction. A new sultone derivative, (E)-ethyl 4-oxo-6-styryl-3,4-dihydro-1,2-oxathiine-5-carboxylate 2,2-dioxide (S-CA), was synthesized and structurally identified by 1 H-NMR, 13 C-NMR, HMQC and X-ray single crystal diffraction analysis. The new rapid synthesis extended the method of ring-closing reaction of sulfonic acid lactone derivatives. The angiogenesis activities of S-CA were evaluated by the chick chorioallantoic membrane (CAM) model. It could selectively suppress small angiogenesis in CAM, without influencing either middle and large angiogenesis. In addition, anticancer efficacy of S-CA was evaluated in vivo using a murine sarcoma S180 model. Reduction of the tumor weight and tumor HE staining regions demonstrated that S-CA (10 mg/kg, intraperitoneal injection) had potent inhibition effects and a 44.71% inhibitory rate in S180 mice. Moreover, an acute toxicity test showed that the LD50 value of S-CA via intraperitoneal injection was 25.624 mg/kg.

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Section: Synthesis Of S-camentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

Yan

Zhang

et al. 2015

Molecules

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“…Sultones are the internal esters of hydroxy sulfonic acids and sulfur analogs of lactones. The biological activities of sultones are concerned with toxicological, skin sensitization, and antiviral properties [13]. In 2009, Majumdar developed a Pd(PPh 3 ) 4 -catalyzed intramolecular C-H arylation reaction of benzenesulfonic acid 2-bromophenyl esters to afford polycyclic sultones, which are generally synthesized by elimination of the corresponding hydroxyl sulfonic acid derivatives, in up to 90% yield (Scheme 3.3, path a) [14].…”

Section: Introductionmentioning

confidence: 99%

Pd‐Catalyzed Synthesis of Oxygen‐Containing Heterocycles

Yang

You

2016

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation

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“…Lactones are cleaved at the acyl-oxygen bond and behave as acylating agents, whereas sultones are cleaved at the carbon-oxygen bond and behave as sulfoalkylating agents. [2][3][4] There are few reports on reactions of 1,3-dienic δ-sultones. [5][6][7] To the best of our knowledge, the reactivity of sultones, especially of 2,4-disubstituted butadiene-1,4-sultones, towards 1,2-and 1,3-binucleophiles has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Reactions of 2,4-diphenyl-butadiene-1,4-sultone with some 1,2- and 1,3-nitrogen bi-nucleophiles

Ali¹,

Jäger²,

Metz³

2015

Arkivoc

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Treatment of 2,4-diphenylbutadiene-1,4-sultone with hydrazine in boiling EtOH gives 1-amino-2,4-diphenyl-1H-pyrrole. On treatment of 2,4-diphenylbutadiene-1,4-sultone with phenyl hydrazine in glacial acetic acid, 4,5-dihydro-5-methyl-1,3,5-triphenyl-1H-pyrazole was isolated. On the other hand, 2,4-diphenylbutadiene-1,4-sultone reacts with 4H-1,2,4-triazol-3-amine and 5-amino-3-phenyl-1H-pyrazole to afford the novel heterocyclic compounds 2-(2,2-dioxo-4-phenyl-3,4-dihydro-8H-

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Recent Developments in the Synthesis and Application of Sultones

Cited by 77 publications

References 126 publications

New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

Pd‐Catalyzed Synthesis of Oxygen‐Containing Heterocycles

Reactions of 2,4-diphenyl-butadiene-1,4-sultone with some 1,2- and 1,3-nitrogen bi-nucleophiles

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