Visible light-induced cyclization reactions for the synthesis of 1,2,4-triazolines and 1,2,4-triazoles.

  title={Visible light-induced cyclization reactions for the synthesis of 1,2,4-triazolines and 1,2,4-triazoles.},
  author={Hongyu Wang and Yanfei Ren and K. Wang and Yunquan Man and Yanan Xiang and Na Li and Bo Tang},
  journal={Chemical communications},
  volume={53 69},
A novel method for concisely synthesizing 1,2,4-triazolines via [3+2] cyclization under visible light is reported. These compounds can be easily converted into 1,2,4-triazoles under basic or photoredox conditions. The application of the 1,2,4-triazoles was also investigated via mild operations. 
15 Citations

Tables from this paper

Visible Light Induced, Metal-free Denitrative Formal [3+2] Cycloaddition for Trisubstituted-Pyrrole Synthesis.

A metal free regioselective synthesis of trisubstituted pyrroles has been developed through a formal [3+2] cycloaddition reaction between 2H-azirines and nitroalkenes under visible light photoredox

Modular 2,3-diaryl-2H-azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization.

A modular 2H-azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization has been developed and can be efficiently converted to various azaheterocycles.

Efficient synthesis of N′-benzylidene-2-hydroxymethylbenzohydrazides from the one-pot reaction of phthalide, hydrazine and aldehydes

We report an efficient, catalyst-free, one-pot synthesis of (E)-N′-benzylidene-2-(hydroxymethyl)benzohydrazide derivatives by the one-pot reaction of phthalide, hydrazine hydrate and aldehyde.

A copper-catalyzed insertion of sulfur dioxide via radical coupling.

Preliminary mechanistic studies indicate that the reaction proceeds through coupling of a sulfonyl radical and α-carbon radical via copper-catalyzed ring-opening C-C bond cleavage of O-acyl oxime and C-N bond Cleavage of 2H-azirine with the insertion of sulfur dioxide.

Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2H-azirines via an SN2'-SN2' cascade in 2-halo-2H-azirines.

This reaction is the first example of substitution at the azirine carbon atom for which an unusual SN2'-SN2' cascade mechanism was revealed.

Visible light-promoted ring-opening functionalization of three-membered carbo- and heterocycles.

By using these strategies, a variety of ring-opening functionalization products, including biologically important carbo- and heterocycles, can be efficiently accessed in a high chemo- and regioselective manner.



One-pot synthesis of 3,4,5-trisubstituted 1,2,4-triazoles via the addition of hydrazides to activated secondary amides.

A general approach has been developed for the one-pot synthesis of 3,4,5-trisubstituted 1,2,4-triazoles from secondary amides and hydrazides via triflic anhydride activation followed by

Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition-oxidative cyclization.

A simple one-step synthesis of 1,2,4-triazole derivatives is provided by a copper-catalyzed oxidative coupling reaction under an atmosphere of air to achieve chemical diversity.

Synthesis of 1,2,4-triazolines and triazoles utilizing oxazolones.

A convenient method for the synthesis of 1,2,4-triazolines using oxazolones and azodicarboxylates is described, which provides efficient access to the corresponding triazoles.

Rapid synthesis of 1,3,5-substituted 1,2,4-triazoles from carboxylic acids, amidines, and hydrazines.

A general method for the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles has been developed from reaction of carboxylic acids, primary amidines, and monosubstituted hydrazines. This highly

I2-Catalyzed Oxidative Coupling Reactions of Hydrazones and Amines and the Application in the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles.

A general and expeditious approach for the metal-free mediated synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from hydrazones and aliphatic amines has been achieved under aerobic oxidative

[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes.

A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from

Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions.

A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved and provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues.

Copper-catalyzed one-pot synthesis of 1,2,4-triazoles from nitriles and hydroxylamine.

A simple and efficient copper-catalyzed one-pot synthesis of substituted 1,2,4-triazoles through reactions of two nitriles with hydroxylamine with inexpensive Cu(OAc)2 as the catalyst is developed and provides a new and useful strategy for synthesis of 1, 2,4 -triazole derivatives.

Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton.

A novel three-component cyclization of 2H-azirines, alkynyl bromides, and molecular oxygen under visible-light photoredox catalysis at room temperature has been developed, which provides a direct