Synthesis of thiazolidin-4-ones via [3+2] cycloaddition of in situ generated aza-oxyallylic cations with isothiocyanates

Wang, Gangqiang; Zhao, Sen; Chen, Rongxing; Yang, Liangfeng; Wang, Jian; Guo, Haibing; Wu, Minghu; Domena, Justin B.; Xing, Yalan; Sun, Shi‐Gang

doi:10.1016/j.tetlet.2017.10.004

Cited by 20 publications

(11 citation statements)

References 30 publications

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“…Almost at the same time, Xing and Sun reported the same method . However in the later report, use of mono‐alkyl substituted α‐halohydroxamate precursor was shown which was not included in the earlier report.…”

Section: [3+2]‐cycloaddition/annulation Reactions With Thiocarbonyls mentioning

confidence: 95%

Recent Developments on the Synthesis of Various Sulfur‐Containing Heterocycles via [3+2]‐ and [4+2]‐Cycloaddition Reactions with Thiocarbonyls

2020

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This minireview summarizes important collection of cycloaddition strategies that were used for the synthesis of sulfur-containing five-and six-membered heterocycles from thiocarbonyl-based synthons. Among various stepwise or concerted methods available to prepare thioheterocycles, cycloaddition reactions of thiocarbonyls in particular present an important class of reaction owing to their ability to function as super dipolarophiles and/or superdienophiles. Design and development of various reactions in recent years with thiocarbonyls have certainly superseded the general purview on this reactive synthon that it often leads to side reaction and oligomerization. This article, apart from including the advances in the known reaction manifold of thiocarbonyls, also provide updates on new developments of cycloaddition chemistry, which includes donor-acceptor (DÀ A) cyclopropanes and azaoxyallyl cation as 1,3-dipolar reaction partners. This review should serve the purpose of an important guiding tool for organic and medicinal chemist to design and develop new class of cycloaddition or related transformations with thiocarbonyls for the preparation of novel heterocycles.

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Section: [3+2]‐cycloaddition/annulation Reactions With Thiocarbonyls mentioning

confidence: 95%

Recent Developments on the Synthesis of Various Sulfur‐Containing Heterocycles via [3+2]‐ and [4+2]‐Cycloaddition Reactions with Thiocarbonyls

2020

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“…With regard to [3+2] cycloaddition processes, azaoxyallyl cation intermediates were key players in syntheses of γ‐lactams, pyrroloindolines,– 1,3‐dihydro‐2H‐pyrrol‐2‐ones,– 4‐imidazolones,– hydantoins, imidazolones, thiazolidin‐4‐ones, and oxazolidin‐4‐ones –…”

Section: α‐Haloamides As a Three‐atom Unit For Concise Synthesis Of Hmentioning

confidence: 99%

The Fascinating Chemistry of α‐Haloamides

et al. 2020

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The aim of this review is to highlight the rich chemistry of α‐haloamides originally mainly used to discover new C−N, C−O and C−S bond forming reactions, and later widely employed in C−C cross‐coupling reactions with C(sp3), C(sp2) and C(sp) coupling partners. Radical‐mediated transformations of α‐haloamides bearing a suitable located unsaturated bond has proven to be a straightforward alternative to access diverse cyclic compounds by means of either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On the other hand, cycloadditions with α‐halohydroxamate‐based azaoxyallyl cations have garnered significant attention. Moreover, in view of the important role in life and materials science of difluoroalkylated compounds, a wide range of catalysts has been developed for the efficient incorporation of difluoroacetamido moieties into activated as well as unactivated substrates.

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“…Our research team has been interested in the development of novel dipolar cycloaddition reactions for the synthesis of biologically active heterocycles . Recently, a new type of azomethine imine dipolar, isatin N,N′ ‐cyclic azomethine imine, has caught our attention due to its unique structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of spiro(indoline‐3,1′‐pyrazolo[1,2‐a]pyrazoles) by 1,3‐dipolar cycloadditions of isatin N,N′‐cyclic azomethine imines with alkynes

Shi

Wang

Chen

et al. 2020

Journal of Heterocyclic Chem

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Synthesis of thiazolidin-4-ones via [3+2] cycloaddition of in situ generated aza-oxyallylic cations with isothiocyanates

Cited by 20 publications

References 30 publications

Recent Developments on the Synthesis of Various Sulfur‐Containing Heterocycles via [3+2]‐ and [4+2]‐Cycloaddition Reactions with Thiocarbonyls

Recent Developments on the Synthesis of Various Sulfur‐Containing Heterocycles via [3+2]‐ and [4+2]‐Cycloaddition Reactions with Thiocarbonyls

The Fascinating Chemistry of α‐Haloamides

Synthesis of spiro(indoline‐3,1′‐pyrazolo[1,2‐a]pyrazoles) by 1,3‐dipolar cycloadditions of isatin N,N′‐cyclic azomethine imines with alkynes

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