Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen

Chemical Communications, Год журнала: 2023, Номер 59(75), С. 11196 - 11199

Опубликована: Янв. 1, 2023

A visible light-driven di-functionalization of maleimide with disulfide and in situ -generated singlet oxygen offers selective 1,2-thiohydroxylation under additive-free conditions.

Язык: Английский

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Modular Assembly of Pyrrolo[3,4-c]isoquinolines through Rh-Catalyzed Cascade C–H Activation/Annulation of O-Methyl Aryloximes with Maleimides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8447 - 8457

Опубликована: Июнь 4, 2024

An efficient and practical strategy for the construction of pyrrolo[3,4-

Язык: Английский

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Rh(III)‐Catalyzed Direct ortho Alkylation of Carbazoles with Nitroalkenes

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(20), С. 3461 - 3466

Опубликована: Авг. 26, 2023

Abstract The Rh(III)‐catalyzed ortho alkylation of N ‐pyridylcarbazoles with nitroalkenes has been developed, furnishing a wide range 2‐(2‐nitroalkyl)carbazoles. Both aromatic and aliphatic participated in this reaction successfully. This protocol also proceeded well an indoline based substrate. Derivatization the representative nitroalkane product was described.

Язык: Английский

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Maleimide‐Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)‐Catalyzed C−H Activation of Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4595 - 4602

Опубликована: Ноя. 1, 2023

Abstract A substrate‐controlled [4+1] annulation of sulfoxonium ylides with maleimides via Rh(III)‐catalyzed C−H bond activation is developed. The reaction 2‐methyl‐ N ‐arylmaleimides in the presence AgNTf 2 diastereoselectively provides diversely functionalized indanonylpyrroline‐2,5‐dione derivatives. Furthermore, AgBF 4 , subsequent leads to biologically intriguing various spiroindanonylpyrroline‐2,5‐diones. This methodology offers a broad substrate scope, good functional group tolerance, and diastereoselectivity.

Язык: Английский

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Catalytic Enantioselective Functionalization of Maleimides: An Update

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(24), С. 3605 - 3622

Опубликована: Ноя. 13, 2024

Comprehensive Summary Maleimide derivatives are well‐established reactive intermediates also found in natural products, synthetic pharmaceuticals and functional polymers. Their specific reactivity widespread applications the field of bioconjugation allowed for development highly selective functionalizations based on simple additions cycloadditions with possible control central C–N axial chirality. These multisite‐reactive scaffolds have aroused a long‐standing interest throughout scientific community more particularly as powerful electrophilic partners recently nucleophilic some transformations. The persistent these easily accessible platforms over last decade has enabled new enantioselective transformations major advancements this presented review. Key Scientists

Язык: Английский

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Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides

The Journal of Organic Chemistry, Год журнала: 2022, Номер 88(1), С. 60 - 74

Опубликована: Дек. 23, 2022

Presented herein is a controllable selective construction of spiro or fused heterocyclic scaffolds through the one-pot cascade reactions 1-phenylpyrazolidinones with maleimides. To be specific, succinimide pyrazolo[1,2-a]pyrazolones were effectively formed via [4 + 1] spiroannulation maleimides simultaneous C(sp2)-H bond activation/functionalization and intramolecular cyclization along traceless fusion pyrazolidinonyl unit into final product. In this reaction, air acts as cost-effective environmentally sustainable oxidant to assist regeneration Rh(III) catalyst. Alternatively, succinimide-fused pyrazolidinonylcinnolines from same starting materials an initial followed by base-promoted skeleton rearrangement in situ product without isolation. Notable features these protocols include easily tunable selectivity, broad substrate scope, oxidant, excellent atom economy, facile scalability.

Язык: Английский

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Rhodium(iii)-catalysed redox neutral alkylation of 3-arylbenzo[d]isoxazoles: easy access to substituted succinimides

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(29), С. 5985 - 5989

Опубликована: Янв. 1, 2023

A convenient method for the alkylation of 3-arylbenzo[d]isoxazoles with maleimides under redox-neutral conditions has been developed, giving a series substituted succinimides in up to 99% yield. This transformation is highly selective give succinimides, and Heck-type products are successfully avoided. protocol features 100% atom-economy broad substrate tolerance, provides novel strategy synthesis diverse an opportunity succinylation protein medication pharmacologists discover first-in-class drugs.

Язык: Английский

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One-Step Syntheses of 3,4-Disubstituted Isochroman-1-ones by the Annulation of Benzoic Acids with Nitroalkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3672 - 3676

Опубликована: Фев. 21, 2024

The Rh(III)-catalyzed annulation of benzoic acids with nitroalkenes was disclosed to afford a wide range 3,4-disubstituted isochroman-1-ones excellent regioselectivity and high catalytic efficiency. Both aromatic aliphatic participated in this cyclization reaction successfully. synthetic value proven by series derivatizations. Furthermore, reliable mechanism is outlined on the basis experimental investigations related precedents.

Язык: Английский

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Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(22), С. 15301 - 15311

Опубликована: Ноя. 2, 2022

A novel protocol for the construction of highly functionalized indolizine derivatives, that is, 1H-pyrrolo[3,4-b]indolizine-1,3-diones (PIZDOs, 3) from 2-(pyridine-2-yl)acetates and maleimides via a regioselective oxidative [3 + 2] annulation was developed. The cascade reaction enabled by heating mixture two substrates in presence Ag2CO3 as an oxidant Cu(OAc)·H2O catalyst chlorobenzene. Consequently, series PIZDOs 3 were synthesized with high regioselectivity moderate yields. This can be used synthesis one-pot rather than through multistep reactions, which is suitable both combinatorial parallel syntheses PIZDOs.

Язык: Английский

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A rhodium-catalyzed cascade C–H activation/annulation strategy for the expeditious assembly of pyrrolidinedione-fused 1,2-benzothiazines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(17), С. 3523 - 3532

Опубликована: Янв. 1, 2024

We have developed a cascade annulation strategy triggered by rhodium( iii )-catalyzed C–H activation for the expeditious assembly of pyrrolidinedione-fused 1,2-benzothiazines from free NH-sulfoximines with maleimides under mild conditions.

Язык: Английский

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