Review of application of the I₂ and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2665 - 2692

Опубликована: Янв. 1, 2024

The synthesis of small molecules and complex scaffolds is one the most important topics in organic synthesis.

Язык: Английский

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Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides

Organic Letters, Год журнала: 2023, Номер 25(40), С. 7298 - 7303

Опубликована: Окт. 3, 2023

An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones iodonium ylides has been developed. The novel strategy allows access to new class of structurally diverse tetrahydro-indolones with high efficiency broad substrate scope. In addition, this transformation represents the first example selective alkenyl C–H bond functionalization enaminones. Finally, potential applications are demonstrated through gram-scale reaction late-stage modification.

Язык: Английский

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Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7214 - 7219

Опубликована: Сен. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Язык: Английский

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Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4833 - 4838

Опубликована: Март 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

Язык: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Год журнала: 2024, Номер 36(1), С. 109799 - 109799

Опубликована: Март 20, 2024

Язык: Английский

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Copper‐Catalyzed Oxidative [1+2+1+2] Cascade Cyclization of N,N‐Dimethyl Enaminones with Benzylamines: A Facile Access to Functionalized 1,4‐Dihydropyridines

Chemistry - A European Journal, Год журнала: 2023, Номер 29(28)

Опубликована: Фев. 24, 2023

Using benzylamines as the C4 source of 1,4-dihydropyridines (1,4-DHPs), a Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for synthesis 1,4-DHPs was firstly developed. A broad range easily available N,N-dimethyl enaminones and are employed smoothly to provide diverse with high efficiency. This method is performed by one-pot C(sp3 )-H bond functionalization/C(sp3 )-N cleavage/cyclization strategy form simultaneously two )-C(sp2 ) bonds, C(sp2 1,4-DHP ring.

Язык: Английский

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I₂-Promoted gem-Diarylethene Involved Aza-Diels–Alder Reaction and Wagner–Meerwein Rearrangement: Construction of 2,3,4-Trisubstituted Pyrimido[1,2-b]indazole Skeletons

Organic Letters, Год журнала: 2023, Номер 25(19), С. 3386 - 3390

Опубликована: Май 8, 2023

A [3 + 1 2] cyclization–rearrangement reaction scheme was developed to synthesize pyrimido[1,2-b]indazoles from aryl methyl ketones, 3-aminoindazoles, and gem-diarylethenes. This metal-free process proceeds via a sequential aza-Diels–Alder Wagner–Meerwein rearrangement, possible mechanism demonstrated based on control experiments. method exhibits good substrate compatibility allows simple conditions. Moreover, the products display significant aggregation-induced emission characteristics after modifications.

Язык: Английский

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Three-Component Chemo-Selective Synthesis of N-(o-Alkenylaryl) Pyrazoles by Pyrazole Annulation and Rh-Catalyzed Chemo-Selective Aryl C–H Addition Cascade

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8619 - 8627

Опубликована: Май 31, 2023

By using readily available enaminones, aryl hydrazine hydrochlorides, and alkynes as starting materials, the chemo-selective three-component synthesis of atropisomeric N-(o-alkenylaryl) pyrazoles has been efficiently accessed with rhodium catalysis. Unlike Satoh-Miura reaction leading to alkyne-based C-H benzannulation by prior prepared N-phenyl substrates, this protocol displays unprecedented selectivity alkenylation blocking second round metal key protonation step in presence acids.

Язык: Английский

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Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(22), С. 5660 - 5666

Опубликована: Янв. 1, 2023

Highly functionalized 3a,7a-dihydroxy hexahydro-4 H -indol-4-ones were efficiently synthesized via a Ru( iii )-catalyzed alkenyl C(sp 2 )–H bond functionalization/[3 + 2] annulation reaction between readily available enaminones and iodonium ylides.

Язык: Английский

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Annulative Nonaromatic Newman–Kwart-Type Rearrangement for the Synthesis of Sulfur Heteroaryls

Organic Letters, Год журнала: 2023, Номер 26(1), С. 46 - 50

Опубликована: Дек. 27, 2023

By employing enaminones and thiuram disulfides as starting materials, the frontiers of Newman–Kwart rearrangement have been expanded to alkenyl system for first time. In addition, instead leading formation simple carbamothioates, has led unprecedented construction S-heteroaryls. Depending on differences in enaminone structure, efficient synthesis functionalized isothiazoles thiophenes achieved.

Язык: Английский

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