17304-69-7

Basic information

• Product Name: Dimethyl 1-phenyl-1H-1,2,3-triazole-4,5-dicarboxylate
• Synonyms: 1-Phenyl-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester
• CAS NO: 17304-69-7
• Molecular Formula: C₁₂H₁₁N₃O₄
• Molecular Weight: 261.23
• Mol File: 17304-69-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Dimethyl 1-phenyl-1H-1,2,3-triazole-4,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 1-phenyl-1H-1,2,3-triazole-4,5-dicarboxylate(17304-69-7)
• EPA Substance Registry System: Dimethyl 1-phenyl-1H-1,2,3-triazole-4,5-dicarboxylate(17304-69-7)

Safety Data

• Hazardous Substances Data: 17304-69-7(Hazardous Substances Data)

Upstream product

• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 622-37-7 Phenyl azide 
• 23055-10-9 1,4-dimethyl but-2-enedioate 
• 108-86-1 bromobenzene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 10181-59-6 2,2,4,4-tetramethyl-3-thioxocyclobutanone 
• 19019-88-6 7-isopropylidene-2,3-dicarbomethoxynorbornadiene 
• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 

Downstream Products

• 129748-83-0 Isopropyl-carbamic acid 5-isopropylcarbamoyloxymethyl-3-phenyl-3H-[1,2,3]triazol-4-ylmethyl ester 
• 143850-03-7 1-Phenyl-4,7-dihydro-1H-[1,2,3]triazolo[4,5-d]pyridazine-5,6-dicarboxylic acid diethyl ester 
• 143850-00-4 4,5-bis(bromomethyl)-1-phenyl-1,2,3-triazole 
• 143850-01-5 4,5-dihydro-4,5-dimethylene-1-phenyl-1,2,3-triazole 
• 92126-29-9 1-phenyl-4,5-bis(hydroxymethyl)-1,2,3-triazole bis(methylcarbamate) 
• 51808-10-7 1-phenyl-4,5-bis(hydroxymethyl)-1,2,3-triazole 

Relevant articles and documents

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Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.

Lewis base catalyzed aerobic oxidative intermolecular azide-zwitterion cycloaddition

The discovery of a novel aerobic oxidative intermolecular azide-zwitterion reaction catalyzed by an organocatalyst is presented. It is demonstrated that the merger of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene and electrondeficient olefins generates reactive zwitterion intermediates, which readily participate in cycloaddition reactions with an array of azides, thus providing facile entry to fully or highly substituted 1,2,3-triazole frameworks. The reaction features an excellent substrate scope, and the products are obtained with high yields and excellent regioselectivities. It is demonstrated that some of these products can be transformed into pharmaceutically important agents. In addition to the experimental results, a detailed mechanistic survey is also provided, including MS studies rationalizing the origin of regioselective control.