Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

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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“…Reagent 779 has also been employed in the synthesis of benzofurans from arynes, incorporating the oxygen from the solvent DMF. 456…”

Section: Sulfur Ylidesmentioning

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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“…Chandrasekhar et al. developed a highly efficient [2+2]/[4+1] cycloaddition cascade of arynes and stable sulfur ylides to synthesize 2‐aroyl benzofurans …”

Section: Figurementioning

confidence: 99%

ZnCl₂‐Catalyzed [4+1] Annulation of Alkylthio‐Substituted Enaminones and Enaminothiones with Sulfur Ylides

Lou

Zhou

et al. 2020

Chemistry A European J

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Concise construction of furan and thiophene units has played an important role in the synthesis of potentially bioactive compounds and functional materials. Herein, an efficient Lewis acid ZnCl 2 catalyzed [4+1] annulation of alkylthio-substituted enaminones is reported, that is, a-oxo ketene N,S-acetals with sulfur ylides to afford 2-acyl-3-aminofuran derivatives. In a similar fashion, [4+1] annulation of the corresponding enaminothiones, that is, a-thioxo ketene N,S-acetals, with sulfur ylides efficiently proceeded to give multisubstituted 3-aminothiophenes. This method features wide substrate scopes as well as broad functional group tolerance, offering a concise route to highly functionalized furans and thiophenes.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…Depending on the electronic nature of the active methylene 51, formal [4+1] cycloaddition with o-quinoid 48 becomes more favorable to generate 2-acyl and 2-aroyl benzofuran derivatives 52 (Scheme 18). Miyabe, 62 Gogoi, 63 and Chandrasekhar 64 expanded the scope of this transformation by employing various active methylenes 51 including chloroacetyls, 2-bromoacetophenones, and sulfonium bromide salts, respectively.…”

Section: Scheme 17 Synthesis Of 2h-chromenes or Coumarins From Arynesmentioning

confidence: 99%

Aryne-Based Multicomponent Coupling Reactions

Ghorai¹,

Lee²

2020

Synlett

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Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

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Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

Cited by 55 publications

References 44 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

ZnCl₂‐Catalyzed [4+1] Annulation of Alkylthio‐Substituted Enaminones and Enaminothiones with Sulfur Ylides

Aryne-Based Multicomponent Coupling Reactions

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Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

Cited by 55 publications

References 44 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

ZnCl2‐Catalyzed [4+1] Annulation of Alkylthio‐Substituted Enaminones and Enaminothiones with Sulfur Ylides

Aryne-Based Multicomponent Coupling Reactions

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Product

Resources

About

ZnCl₂‐Catalyzed [4+1] Annulation of Alkylthio‐Substituted Enaminones and Enaminothiones with Sulfur Ylides