Silver(I)‐ and Base‐Mediated formal [4+3] Cycloaddition of in Situ generated 1,2‐Diaza‐1,3‐dienes with C,N‐Cyclic Azomethine Imines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(13), С. 2626 - 2631

Опубликована: Май 6, 2020

Abstract A silver(I)‐ and base‐mediated formal [4+3] cycloaddition reaction of in situ generated 1,2‐diaza‐1,3‐dienes with formed C,N ‐cyclic azomethine imines has been developed. This protocol provided an efficient method for the synthesis biologically important 1,2,4,5‐tetrazepine derivatives a wild substrate scope excellent functional group tolerance moderate to yields. magnified image

Язык: Английский

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A Facile Approach to Benzosultam‐fused 4‐Imidazolidinone Derivatives from N‐Sulfonyl Ketimine and α‐Halogenated Hydroxamates

ChemistrySelect, Год журнала: 2022, Номер 7(4)

Опубликована: Янв. 24, 2022

Abstract The novel benzosultam‐fused 4‐imidazolidinone scaffold was constructed by a concise [3+2] annulation reaction of α‐halogenated hydroxamates and N‐sulfonyl ketimine for the first time. transformation proceeded smoothly under mild transition‐metal‐free conditions in moderate to excellent yields (up 95 %). Moreover products are potentially useful promising medicinal research.

Язык: Английский

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Synthesis of 2‐Alkenyl‐4H‐3,1‐Benzoxazin‐4‐Ones through HFIP‐Mediated Decarboxylative [4+2]‐Annulation of Isatoic Anhydrides with Cyclopropenones under Silver Catalysis

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(16), С. 4085 - 4090

Опубликована: Июнь 25, 2021

Abstract We herein describes an HFIP‐mediated [4+2]‐cycloaddition reaction from simple and easily available isatoic anhydrides cyclopropenones under silver catalysis. This transformation involves the tandem decarboxylative esterification, intermolecular addition, intramolecular substitution, small ring opening isomerization processes, which allows rapid assembly of versatile 2‐diarylalkenyl‐4 H ‐3,1‐benzoxazin‐4‐ones. magnified image

Язык: Английский

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Stereoselective [4+3]-Cycloaddition of 2-Amino-β-nitrostyrenes with Azaoxyallyl Cations to Access Functionalized 1,4-Benzodiazepin-3-ones

Molecules, Год журнала: 2024, Номер 29(6), С. 1221 - 1221

Опубликована: Март 8, 2024

The 1,4-benzodiazepine structural framework is a fascinating element commonly found in biologically active and pharmaceutically relevant compounds. A highly efficient method for synthesizing 1,4-benzodiazepin-3-ones described, involving [4+3]-cycloaddition reaction between 2-amino-β-nitrostyrenes α-bromohydroxamate, with Cs2CO3 used as base. This process yielded the desired 1,4-benzodiazepines good yields. Furthermore, an organocatalytic asymmetric was successfully accomplished using bifunctional squaramide-based catalyst. approach enabled enantioselective synthesis of chiral commendable yields moderate enantioselectivities, reaching up to 80% yield 72% ee.

Язык: Английский

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Cascade Annulation for Synthesizing Chromenopyrrolones from o-Hydroxyphenyl Enaminones and 2-Halo-N-alkyloxyacetamides

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 27, 2024

A cascade cyclization reaction comprising two halogenation reactions and a Michael addition was developed for the synthesis of chromeno[2,3-

Язык: Английский

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Facile Synthesis of Functionalized 1,4‐Benzodiazepine‐3‐One‐5‐Acetates via [4 + 3]‐Annulation of Azaoxyallyl Cations With 2‐Aminophenyl α,β‐Unsaturated Esters

Bulletin of the Korean Chemical Society, Год журнала: 2020, Номер 41(7), С. 727 - 734

Опубликована: Июль 1, 2020

A metal‐free [4 + 3]‐annulation of α‐halohydroxamates with 2‐aminophenyl α,β‐unsaturated esters has been developed for the construction seven‐membered 1,4‐benzodiazepine‐3‐one‐5‐acetates in moderate to good yields (up 82% yield). The annulation involved cascade reaction an generation azaoxyallyl cation, aza‐addition this and intramolecular aza‐Michael yield 1,4‐benzodiazepine‐3‐one‐5‐acetates.

Язык: Английский

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Synthesis of thiazolidin-4-ones from α-enolic dithioesters and α-halohydroxamates

New Journal of Chemistry, Год журнала: 2021, Номер 45(32), С. 14508 - 14512

Опубликована: Янв. 1, 2021

A facile access to thiazolidin-4-ones from α-enolic dithioesters and α-halohydroxamates in situ derived active 1,3-dipolar aza-oxyallyl cations was achieved under mild conditions.

Язык: Английский

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One‐Pot Synthesis of Fused Indolin‐3‐Ones via a [3+3] Cycloaddition Reaction

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(22), С. 5092 - 5098

Опубликована: Сен. 8, 2021

Abstract A formal [3+3] cycloaddition reaction of azaoxyallyl cations and isatogens generated in situ from α ‐halo hydroxamates o ‐nitroalkynes, respectively, was developed. The cycloisomerization the followed by base‐mediated elimination hydrogen halide 1,3‐dipolar with isatogen intermediates, were hallmarks this one‐pot tandem reaction. series tricyclic fused indolin‐3‐ones obtained under very mild conditions high atom economy, exhibited excellent functional group tolerance. In addition, highly scalable to multigram quantities. robust DNA staining patterns agarose gel electrophoresis. Coupled fluorescence properties products, these results highlight potential utility various cell‐staining applications. magnified image

Язык: Английский

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Synthesis of spirocyclic oxazole derivatives from 2-arylidene cycloalkanones and α-halohydroxamates

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(21), С. 4293 - 4297

Опубликована: Янв. 1, 2022

A facil route to spirocyclic oxazole derivatives via the [3 + 2] cycloaddition reactions between 2-arylidene cycloalkanones and azaoxyallyl cations was developed.

Язык: Английский

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[8+3]‐Cycloaddition Reactions of Heptafulvenes or Azaheptafulvenes with α‐Halohydroxamates

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(7)

Опубликована: Май 12, 2022

Abstract The base‐mediated higher‐order [8+3]‐cycloaddition reactions of heptafulvenes or azaheptafulvenes with α‐halohydroxamates have been achieved under mild and metal‐free conditions. These do not only provide a direct route for the synthesis highly functionalized cycloheptatriene‐fused piperidinones piperazinones in moderate to excellent yields, but they also enrich chemistry azaheptafulvenes. Furthermore, gram‐scale further derivatizations demonstrated synthetic potential these cycloaddition reactions.

Язык: Английский

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