1198613-79-4

Upstream product

• 1198612-95-1 C₁₀H₁₀BrN₃ 
• 1248676-97-2 4-bromo-2-ethyl-2H-1,2,3-triazole 
• 98-80-6 phenylboronic acid 
• 1680-44-0 4-phenyl-1H-1,2,3-triazole 
• 105-58-8 Diethyl carbonate 
• 536-74-3 phenylacetylene 
• 74-96-4 ethyl bromide 
• 1135539-10-4 1-(methylsulfonyl)-4-phenyl-1H-1,2,3-triazole 

Relevant academic research and scientific papers

Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air

We developed a highly regioselective base-induced synthesis of N2-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an SN2-like mechanistic pathway to explain the high N2-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72–90%).

Ruthenium-Catalyzed meta-Selective C?H Nitration of Biologically Important Aryltetrazoles

The first example of tetrazole-directed meta-selective C?H nitration is described. This transformation provided a straightforward approach for the synthesis of biologically important m-nitroaryltetrazoles in moderate to excellent yields with good functional group compatibility. In addition, new metallo-β-lactamase inhibitors were obtained by further transformation of the synthesized m-nitroaryltetrazoles. (Figure presented.).

Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition

Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

General solution to the synthesis of N-2-substituted 1,2,3-triazoles

The regioselective N-alkylation of 1,2,3-triazoles 1 - 6 was studied. Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5- trimethylsilyl-1,2,3-triazoles. These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10 - 15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds.

Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: Efficient synthesis of poly-substituted 1,2,3-triazoles

"Chemical Equation Presented" Reaction of 4-bromo-NH-1,2,3- triazoles 2 with alkyl halides In the presence of K2CO3 in DMF produced the corresponding 2-substituted 4-bromo1,2,3-triazoles 5 In a regioselective process. Subsequent Suzuki cross-coupling reaction of these bromides provided an efficient synthesis of 2,4,5-trisubstituted triazoles 3. In addition, reduction of the bromotriazoles by hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles 8.