Photocatalytic synthesis of 2,3-diamines from anilines and DIPEA via C–N bond cleavage and C–C bond formation

Green Chemistry, Год журнала: 2023, Номер 26(1), С. 300 - 305

Опубликована: Дек. 5, 2023

2,3-Diamines are skeleton structures widely found in natural products and drug molecules can also be used as ligands transition metal catalysis.

Язык: Английский

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Aza-Povarov Reaction. A Method for the Synthesis of Fused Tetracyclic Chromeno[4,3-d]pyrido[1,2-a]pyrimidines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 1099 - 1107

Опубликована: Янв. 4, 2024

A cornerstone in drug discovery is the development of strategies to provide privileged small molecules with specific structural and stereochemical complexity, allowing access new potential therapeutic entities. In this work, a strategy based on [4 + 2] Povarov reaction involving 1,3-diazadiene was developed. This approach applied for straightforward procedure preparation chromeno[4,3-d]pyrido[1,2-a]pyrimidine derivatives, accessible substrates, 2-aminopyridine unsaturated aldehydes, excellent atom economy obtain four fused ring heterocycles, regio- diastereoselective way.

Язык: Английский

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Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1430 - 1435

Опубликована: Янв. 23, 2024

Abstract A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2 H ‐chromen‐2‐ones using N ‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights special roles which were not only used reactants but also an internal oxidant selectively activated ‐ α ‐C( sp 3 )−H bond. reaction features catalyst‐free, broad substrate scopes ( 27 examples 24 examples), operationally simple for one‐step synthesis, recovery recycling solvent.

Язык: Английский

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Oxidative Dehydrogenative Coupling of Arylamines with N-allyl and N-vinylamines for the Synthesis of Quinolines and 2-Methylquinoline Derivatives

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134450 - 134450

Опубликована: Янв. 1, 2025

Язык: Английский

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Multicomponent one-pot construction of benzo[f]quinoline-linked covalent organic frameworks for H2O2 photosynthesis

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 12, 2025

The exploration of stable and functional linkages by multicomponent reactions to enrich the stability diversity covalent organic frameworks (COFs) broaden their potential applications is fundamental significance development COFs. Herein, we report facile construction a set benzo[f]quinoline-linked COFs (B[f]QCOFs) via one-pot three-component [4 + 2] cyclic condensation aldehydes aromatic amines with easy-to-handle triethylamine as vinyl source. These B[f]QCOFs possess high crystallinity, good physico-chemical well significant light absorption ability. More importantly, obtained B[f]QCOF-1 exhibits superior H2O2 production rate 9025 μmol g-1 h-1 in pure water without any sacrificial agent under visible-light irradiation, surpassing most previously reported COF-based photocatalysts comparable conditions. This work not only provides general synthetic route for preparation fully conjugated COFs, but also helps rational design efficient photosynthesis.

Язык: Английский

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Metallaphotocatalytic synthesis of anilines through tandem C–N transposition and C–H alkylation of alkylamines

Nature Synthesis, Год журнала: 2023, Номер 2(12), С. 1171 - 1183

Опубликована: Июль 27, 2023

Язык: Английский

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Mg(II)‐Catalyzed [4+2] Annulation for the Synthesis of 2‐Arylquinoline Motifs: Applications and DFT Studies

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 366(6), С. 1382 - 1387

Опубликована: Дек. 9, 2023

Abstract Mg‐catalyzed [4+2] cycloaddition reactions between 2‐aminobenzaldehydes and ynones offered an array of 2‐arylquinoline motifs merged with a CF 3 ‐acyl group. Furthermore, annulation as the key step, DDD107498, DDD102542, Hit analogues were assembled. Finally, computational study reaction mechanism was conducted.

Язык: Английский

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TBHP Mediated C–N Bond Cleavage of Tertiary Amines toward the Synthesis of Oxalamides and α,β-Epoxy Amides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1524 - 1533

Опубликована: Янв. 11, 2024

An efficient and convenient method for the synthesis of oxalamides by reaction β-ketoamides with tertiary amines TBHP was developed. A variety substrates were well-tolerated in this transformation. Based on control experiments, a plausible mechanism proposed that involved tandem oxidation/amination process. In addition, α,β-epoxy amides could be obtained adjusting conditions.

Язык: Английский

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Benzannulation with Et₃N as 1,3-Diene Variants

Organic Letters, Год журнала: 2023, Номер 25(43), С. 7775 - 7779

Опубликована: Окт. 24, 2023

With triethylamine as a 1,3-diene variant, simple and practical process for the synthesis of phthalimides has been developed from readily available maleimide. The transformation can be performed in absence metal catalyst with high levels functional group tolerance. Various phthalimide compounds were constructed moderate to good yields under mild conditions. Mechanism research indicates that oxygen acid also play crucial roles this reaction.

Язык: Английский

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Scope and Mechanistic Studies on the Ruthenium-Catalyzed Multicomponent Deaminative C–H Coupling Reaction of Phenols with Aldehydes and Enamines for the Formation of Xanthene and Dioxacyclic Derivatives

ACS Catalysis, Год журнала: 2023, Номер 13(13), С. 9051 - 9063

Опубликована: Июнь 23, 2023

The in situ generated catalytic system from the tetranuclear Ru–H complex [(PCy3)(CO)RuH]4(O)(OH)2 (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) has been found to mediate a multicomponent deaminative coupling reaction of phenols aldehydes and enamines form xanthene products. C–H 2-hydroxybenzaldehydes cyclic efficiently installed tricyclic 1,3-dioxacin derivatives, while analogous triethylamine selectively formed bicyclic 1,5-dioxacyclic derivatives. density functional theory (DFT) calculations established two energetically viable mechanistic pathways for formation products, which both identified C–O bond cleavage step as turnover limiting step. A Hammett plot 3,5-dimethoxyphenol an enamine para-substituted benzaldehydes p-X-C6H4CHO (X = OMe, Me, H, Cl, CF3) showed negative slope (ρ −0.98). calculated energy analysis similar trend −0.59) mechanism via rate-limiting combined experimental DFT computational results support path that involves dehydrative phenol aldehyde, followed by forming product.

Язык: Английский

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