Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер 35(11), С. 109683 - 109683

Опубликована: Март 2, 2024

Язык: Английский

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Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2505 - 2515

Опубликована: Фев. 5, 2024

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means synthesizing variety fully substituted thiazoles by constructing C–C(CO), C–S, and C–N bonds. This transformation allows the realization unusual aryl C2 synthons simultaneously thioylation dicarbonylation sites. preliminary mechanistic study performed indicated that cleavage C═C bonds involves bicyclization/ring-opening oxidative coupling sequence.

Язык: Английский

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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2363 - 2369

Опубликована: Март 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

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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Chemodivergent Synthesis of Benzofurans and 2,3‐Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(15), С. 1727 - 1733

Опубликована: Март 26, 2024

Comprehensive Summary Chemodivergent synthesis of benzofurans and 2,3‐dihydrobenzofurans has been realized. Under a reaction system consisting DBDMH K 2 CO 3 as promotors, controlled conditions enabled the formation two sets valuable heterocycles from tandem transformation enaminones salicylaldehydes. The key to success was identification parameters, in which imine intermediate formed by transient halogenation coupling substitution processes underwent either aldol condensation/annulation or hydrolysis/aldol condensation. additives NH 4 Cl Fe (SO ) unique selectivity this reaction. A broad substrate scope salicylaldehydes employed reaction, demonstrating excellent functional group tolerance versatility.

Язык: Английский

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Photocatalytic Pyridine Synthesis with Enaminones and TMEDA under Metal-Free Conditions

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 11060 - 11066

Опубликована: Июль 24, 2024

Reported herein is a new photocatalytic annulation for the synthesis of 2,3,4,6-tetrasubstituted pyridines with enaminones and N,N,N′,N′-tetramethyl ethylenediamine (TMEDA). The reactions take place without requiring transition metal reagent provide products broad scope. methyl in TMEDA acts as carbon source pyridine ring construction, BrCF2CO2Et plays role terminal oxidant free radical quenching.

Язык: Английский

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Tunable Synthesis of 4-Acyl- and 4-Formyl Pyrroles by Rhodium-Catalyzed Ring-Expansion of Azirines with Enaminones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 19, 2025

A rhodium-catalyzed annulation of 2H-azirines with enaminones is presented. This protocol affords a convenient approach to the diversity-oriented synthesis 4-acyl- and 4-formyl pyrroles good functional group tolerance. The utility this reaction has been demonstrated by scale-up preparation, late-stage modification natural molecules, diverse derivatives.

Язык: Английский

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Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation

Synthesis, Год журнала: 2024, Номер 56(16), С. 2565 - 2571

Опубликована: Апрель 26, 2024

Abstract Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S C–N bond formation by running under air atmosphere at ambient temperature. Broad substrate tolerance the sustainable protocol has verified practical synthesis divergent thiazoles with both monocyclic fused cyclic structures.

Язык: Английский

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Oxidative Free-Radical C(sp²)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8521 - 8530

Опубликована: Июнь 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Язык: Английский

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Transition-Metal-Free C–H Trifluoromethylthiolation of N,N-Disubstituted Enaminones To Access CF₃S-Functionalized Enaminones and Their Application in the Synthesis of CF₃S-Heteroaryls

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 9078 - 9085

Опубликована: Июнь 3, 2024

The α-C–H trifluoromethylthiolation of N,N-disubstituted enaminones has been achieved with simple and cheap CF3SO2Na as the CF3S source. reactions were run at mild temperature (0 °C to rt) using POCl3 only reducing reagent. work represents first example on synthesis α-trifluoromethylthio via direct C–H functionalization. In addition, resulting CF3S-functionalized have proven useful building blocks in various heteroaromatic compounds by annulation reactions.

Язык: Английский

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