The α-alkylation of carbonyl sulfoxonium ylides: studies and applications in the synthesis of new sulfur heterocycles

Jesus, Matheus Pereira de; Echemendía, Radell; Burtoloso, Antonio C. B.

doi:10.1039/d3qo00688c

Cited by 6 publications

(2 citation statements)

References 51 publications

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“…Very recently, the S-H insertion reaction of 2-aminothiophenol with α-alkylated sulfoxonium ylides has been employed for the synthesis of 1,4-benzothiazin-3-one derivatives in a 42-78% yield (Figure 2, path f). The reaction was run in acetonitrile at 60 • C for 48 h, leading to the products in 42-78% yields [48].…”

Section: Other Synthetic Routesmentioning

confidence: 99%

The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue

Alfieri,

Panzella

2023

Molecules

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1,4-Benzothiazines are the main building blocks of the naturally occurring pheomelanin pigments, and their chromophoric properties have been strongly related to the well-known phototoxicity of these pigments, partly responsible for the high incidence of melanoma and other skin cancers in red-haired people. However, some peculiar features of the 1,4-benzothiazine chromophore could be functionally exploited in several sectors. Within this context, in this perspective, an overview of the very recently reported applications of the 1,4-benzothiazine chromophore in pH sensing, filter permeability control, smart packaging, electrochromic device fabrication, bioimaging, photocatalysis, and HPLC detection systems is provided, together with a brief presentation of recently developed synthetic approaches to the 1,4-benzothiazine scaffold, with the aim of emphasizing the still-undervalued multifunctional opportunities offered by this class of compounds.

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Section: Other Synthetic Routesmentioning

confidence: 99%

The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue

Alfieri,

Panzella

2023

Molecules

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“…To investigate the mechanism for the [3 + 3] annulation, we performed the reaction of sulfoxonium ylide with ynone at 10 °C; the reaction yielded dienyl sulfoxonium ylide 8 which was confirmed by NMR and HRMS analysis (Scheme d). , This ylide 8 underwent annulation to give m -terphenyl adduct 3a at rt and gave paraben derivative 4a using TMSOTf. When we performed the reaction using keto-derived vinyl sulfoxonium ylide the reaction gave thiabenzene derivative 9 …”

mentioning

confidence: 98%

Divergent Approach to Highly Substituted Arenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Ynones

Davas,

Gopalakrishnan,

Bar

et al. 2023

Org. Lett.

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Revisiting the Reaction of Sulfur Ylides with Acetylenic Esters: Synthesis of Trisubstituted 1,3‐Dienes, α‐Carbonyl Vinyl Sulfoxides and α‐Carbonyl Vinyl Sulfoxonium Ylides

de Jesus,

Burtoloso

2024

Chemistry An Asian Journal

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We report herein a reexamination of the reactions between sulfoxonium ylides and acetylenic esters. Continuing our previous study of conjugate additions using α‐carbonyl sulfoxonium ylides, we came across an interesting transformation when dimethyl acetylenedicarboxylate (DMAD) was employed as a Michael acceptor. Trisubstituted electron‐deficient 1,3‐dienes and α‐carbonyl vinyl sulfoxides were obtained for the first time from these sulfur ylides, in a stereoselective manner (exclusively forming the E‐isomer), achieving yields of up to 70 % and 83 %, respectively. Selected dienes were subsequently utilized in the synthesis of novel nitrogen heterocycles. Interestingly, when di‐tert‐butyl acetylenedicarboxylate (DtBAD) or alkyl propiolates were evaluated, the isolated product arose from the classical Michael addition, yielding α‐carbonyl vinyl sulfoxonium ylides in yields of up to 89 %.

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The α-alkylation of carbonyl sulfoxonium ylides: studies and applications in the synthesis of new sulfur heterocycles

Abstract: The challenging direct α-alkylation of sulfoxonium ylides is demonstrated after a deep study with several electrophiles. Twenty-five alkylated ester-sulfoxonium ylides could be prepared in yields up to 67%, employing Michael...

Cited by 6 publications

References 51 publications

The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue

The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue

Divergent Approach to Highly Substituted Arenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Ynones

Revisiting the Reaction of Sulfur Ylides with Acetylenic Esters: Synthesis of Trisubstituted 1,3‐Dienes, α‐Carbonyl Vinyl Sulfoxides and α‐Carbonyl Vinyl Sulfoxonium Ylides

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