Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions

Chemical Reviews, Год журнала: 2021, Номер 121(23), С. 14555 - 14593

Опубликована: Сен. 29, 2021

Triazines are an important class of six-membered aromatic heterocycles possessing three nitrogen atoms, resulting in types regio-isomers: 1,2,4-triazines (a-triazines), 1,2,3-triazines (v-triazines), and 1,3,5-triazines (s-triazines). Notably, the application triazines as cyclic aza-dienes inverse electron-demand Diels–Alder (IEDDA) cycloaddition reactions has been established a unique powerful method N-heterocycle synthesis, natural product preparation, bioorthogonal chemistry. In this review, we comprehensively summarize advances construction these via annulation ring-expansion reactions, especially emphasizing recent developments challenges. The synthetic transformations focused on IEDDA which have allowed access to wide scope heterocycles, including pyridines, carbolines, azepines, pyridazines, pyrazines, pyrimidines. utilization triazine key steps synthesis is also discussed. More importantly, particular attention paid fast click ligation with various strained alkenes alkynes, opens new opportunity for studying biomolecules chemical biology.

Язык: Английский

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Selective Radical Transformations with Aryldiazonium Salts

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(12)

Опубликована: Фев. 15, 2023

Abstract This review provides an overview of the use aryldiazonium salts as source aryl radicals and their application in development selective transformations over last 13 years. Examples were organized under thermal photocatalytic transformations. accessible follow‐up this field for both radical catalytic chemists working industry well academia.

Язык: Английский

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Copper-Catalyzed Trifluoromethylthio-arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide

Organic Letters, Год журнала: 2022, Номер 24(5), С. 1207 - 1212

Опубликована: Янв. 31, 2022

A copper-catalyzed four-component trifluoromethylthio-arylsulfonylation between styrene derivatives, AgSCF3, aryldiazonium tetrafluoroborates, and ex situ generated sulfur dioxide (from SOgen) is presented. This reaction features mild conditions, good functional group tolerance, a broad substrate scope, yields, excellent diastereoselectivity. Preliminary mechanistic studies revealed that radical process might be involved in this transformation.

Язык: Английский

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Cu‐Catalysed Three‐Component Reaction of Aryldiazonium Salts with Fluorinated Diazo Reagents and Nitriles: Access to Difluoro‐ and Trifluoromethylated N¹‐Aryl‐1,2,4‐triazoles

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(20), С. 4432 - 4437

Опубликована: Авг. 10, 2020

Abstract A copper‐catalysed three‐component reaction of aryldiazonium salts with fluorinated diazo reagents and nitriles is described. This formal [1+2+2] annulation protocol provides rapid access to a diverse array difluoro‐ trifluoromethylated N 1 ‐aryl‐1,2,4‐triazoles under simple conditions. The synthetic applicability divergent drug‐like 1,2,4‐triazoles also demonstrated. magnified image

Язык: Английский

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Transition-metal free C–N bond formation from alkyl iodides and diazonium salts via halogen-atom transfer

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Дек. 27, 2022

Construction of C-N bond continues to be one part the most significant goals in organic chemistry because universal applications amines pharmaceuticals, materials and agrochemicals. However, E2 elimination through classic S

Язык: Английский

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Regioselective Synthesis of N²-Aryl 1,2,3-Triazoles via Electro-oxidative Coupling of Enamines and Aryldiazonium Salts

Organic Letters, Год журнала: 2022, Номер 24(6), С. 1274 - 1279

Опубликована: Фев. 3, 2022

An efficient synthetic route for the construction of N2-aryl 1,2,3-triazoles is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates aryldiazonium salts were used as starting materials, developed protocol displays excellent functional group tolerance, allowing an extensive range substrate scope up to 91% isolated yield. Various mechanistic studies, along with isolation intermediate adduct, refer successive ionic radical reaction sequences.

Язык: Английский

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Aryldiazonium-Salt-Triggered Carboxylative Azotization of Pyrroles or Indoles with Polyhalomethanes via Halogen-Atom Transfer (XAT)

Organic Letters, Год журнала: 2024, Номер 26(2), С. 461 - 466

Опубликована: Янв. 4, 2024

A halogen-atom-transfer (XAT)-based method for carbonylazotization of pyrroles or indoles with aryldiazonium salts and polyhalomethanes via dual C(sp2)–H bond functionalization is described. Using realizes carbonylation/azotization polyhalomethyl-radical-mediated electrophilic substitution, thus providing a green, efficient, step-economy approach synthesis multifunctional from the easily available substrates. Notably, this strategy relies on use to extend well-established iodine atom transfer bromine chlorine transfer.

Язык: Английский

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Enantioselective Arylcyanation of Styrenes viaCopper‐Catalyzed Radical Relay^†

Chinese Journal of Chemistry, Год журнала: 2020, Номер 39(1), С. 50 - 54

Опубликована: Сен. 27, 2020

The first copper‐catalyzed enantioselective arylcyanation of styrenes has been developed using readily available anilines as aryl radical precursors under mild conditions, which enables easy access to chiral 2,3‐diaryl propionitriles with moderate good enantioselectivities. This operationally straightforward reaction exhibits broad substrate scope and functional group tolerance. Notably, this method applied the synthesis AIEgen well estrogen receptor‐β agonist ( R )‐diarylpropionitrile (DPN).

Язык: Английский

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Base-Promoted (3 + 2) Cycloaddition of Trifluoroacetohydrazonoyl Chlorides with Imidates En Route to Trifluoromethyl-1,2,4-Triazoles

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14514 - 14522

Опубликована: Окт. 20, 2022

A base-mediated (3 + 2) cycloaddition of trifluoroacetohydrazonoyl chlorides with imidates for the construction 3-trifluoromethyl-1,2,4-triazoles has been described. This reaction is characterized by readily starting materials, simple conditions, good yields, a broad substrate scope, and excellent regioselectivity. The utility this protocol validated synthesis drug-like molecule.

Язык: Английский

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Advances in Tetrazole Synthesis – An Overview

ChemistrySelect, Год журнала: 2022, Номер 7(29)

Опубликована: Авг. 3, 2022

Abstract Most of the active pharmaceutical ingredients (API) contain tetrazole ring, thus making them vast significance in new drug design descriptors. With this importance view, enormous studies are being carried out on synthesis derivatives. The methods its [3+2] cycloaddition, multicomponent reactions, microwave‐assisted using heterogeneous and homogeneous catalysts. Hence, it is necessary to highlight green catalysis that would be more environmentally benign economically viable. In review, we discuss processes presence These catalytic materials gave higher product yield a shorter reaction time were reusable.

Язык: Английский

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