501074-32-4

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 693-02-7 hex-1-yne 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1312297-92-9 C₂₃H₂₇NO₃S 
• 1591958-24-5 N-[(1Z)-1-(dimethylamino)-3-oxohept-1-en-2-yl]-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Deoxygenative C2-heteroarylation of quinoline N-oxides: Facile access to α-Triazolylquinolines

A metal-and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-Triazoles. A variety of α-Triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.

Rhodium(II)-Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)-Aurantioclavine

An efficient rhodium(II)-catalyzed [4+3] cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed. Azepino[5,4,3- cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good

Facile synthesis of pyrroloindoles: Via a rhodium(II)-catalyzed annulation of 3-benzylidene-indolin-2-ones and α-imino carbenes

The annulation of 3-benzylidene-indolin-2-ones with α-imino rhodium carbenes generated in situ from N-sulfonyl-1,2,3-triazoles is presented. Through the appropriate choice of catalyst, the reactions can be reasonably modulated, and consequently, a number of pyrroloindole derivatives were constructed in moderate to excellent yields.

Rhodium-Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine-Type Amaryllidaceae Alkaloids

Rhodium-catalyzed denitrogenative [3+2] cycloaddition of 1-sulfonyl-1,2,3-triazoles with cyclic silyl dienol ethers has been developed for the synthesis of functionalized hydroindolones or their corresponding silyl ethers. The present method has been employed to construct synthetically valuable bicyclo[3.3.1]alkenone derivatives and pyrrolidine-ring-containing bicyclic indole compounds. As a further synthetic application, a stereoselective synthesis of 5,11-methanomorphanthridin-3-one, which shares a key skeleton with montanine-type Amaryllidaceae alkaloids has been achieved by using this chemistry.

DABCO/AcOH Jointly Accelerated Copper(I)-Catalysed Cycloaddition of Azides and Alkynes on Water at Room Temperature

An expeditious room temperature protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal alkynes and substituted azides has been achieved using the combination of CuSO4-ascorbate/1,4-diazabicyclo[2.2.2]octane/acetic acid. This expeditious protocol is applicable to aryl, alkyl, and sulfonyl azides. Acetic acid accelerates the protonation of cuprated triazole and thus avoids the possible side reactions. Devoid of acetic acid, the reaction pathway alters to the ketinimine route and results in the formation of sulfonamides.

Rhodium(II)-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with 2H-azirines: A new method to dihydropyrazines

An efficient rhodium(II)-catalyzed transannulation method of 1-sulfonyl-1,2,3-triazoles with 2H-azirines has been utilized for the synthesis of phenyl-substituted dihydropyrazines. The dihydropyrazine products can be further converted to pyrazines under b

Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles and epoxides: Regioselective synthesis of substituted 3,4-dihydro-2 H-1,4-oxazines

Rhodium-catalyzed transannulation of 1,2,3-triazoles and ring-opening reactions of epoxides is described. A number of 3,4-dihydro-2H-1,4-oxazines are obtained in moderate yields probably involving generation of α-imino rhodium(II) carbene species.

Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates

In this article, a combination of Cu(OAc)2·H 2O/2-aminophenol was developed as a highly efficient and controlling catalytic system for sulfonyl azids involved CuAAC. By using this catalytic system, sulfonyl azids reacted with normal

Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes

The first transannulation of 1,2,3-triazoles with terminal alkynes into pyrroles is reported. The reaction proceeds in the presence of a Rh 2(oct)4/AgOCOCF3 binary catalyst system providing a straightforward approach to 1,2,4-trisubstituted pyrroles in good to excellent yields.