1,2,3-Triazole

changed changed 477202367 1H-1,2,3-Triazole-2D-numbering.svg skin-invert-image 100px 1%2C2%2C3-Triazole3d.png bg-transparent 100px 1H-1,2,3-Triazole 1,2,3-Triazole changed ?? 288-36-8 correct FDA EM7554254W correct chemspider correct EBI 35566 60839 608-262-3 67516 1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) c1cnn[nH]1 QWENRTYMTSOGBR-UHFFFAOYAF correct chemspider 1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) correct chemspider QWENRTYMTSOGBR-UHFFFAOYSA-N C1=CN=NN1 C2H3N3 69.0654 colorless liquid 1.192 23 to 25 203 very soluble 9.41984 1,2,3-triazole - an overview https://www.sciencedirect.com/topics/chemistry/1-2-3-triazole Comprehensive Heterocyclic Chemistry 1.2 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 1,2,4-triazole imidazole 1,2,3-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic aromatic heterocycle.Heterocyclic chemistry T.L. Gilchrist Prentice Hall Press 1987 0-582-01421-2 Synthesis The unsubstituted ring can be produced by an oxidative coupling of glyoxal, hydrazine and sodium nitrite.Song Lei Ang Hwee Ting Senthilperumal Jagadeesan Kanusu Umamaheswara Rao Venugopal Sivasankaran Rangarajan Naveen Krishnamoorthy Shivasankar Dubbaka Srinivas Reddy O’Neill Patrick Wu Jie 1,2,3-Triazole Synthesis: Development of Safe and Effective Batch and Continuous Manufacturing Processes Organic Process Research & Development 12 March 2024 10.1021/acs.oprd.4c00020 A wide range of methods exist for forming substituted 1,2,3-triazoles.Krivopalov Victor P Shkurko Oleg P 1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring Russian Chemical Reviews 30 April 2005 74 4 339–379 10.1070/RC2005v074n04ABEH000893 free These include the Banert cascade or the azide alkyne Huisgen cycloaddition in which an azide and an alkyne undergo a 1,3-dipolar cycloaddition reaction. Under thermal conditions, regioselectivity is substrate dependent. Selectivity can be increased with metal catalysts, which have the added benefit of reacting without excessive or extensive heating. Copper catalyzed cycloadditions favor 1,4-disubstituted triazoles, Ruthenium catalyzed cycloaddition favor 1,5-disubstituted triazoles. This chemistry was expanded by Zhu et al. in 2018 wherein they report a two-step sequence from a terminal alkyne to 4-cyano 1,5-disubstituted triazoles. Liu P. Clark R. Zhu L. Synthesis of 1‑Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4‑Cyano-1,2,3-triazoles J. Org. Chem. 2018 83 9 5092–5103 10.1021/acs.joc.8b00424 29630830 Properties The 2H-1,2,3-triazole tautomer is the major form in aqueous solution. Adrien Albert Peter J. Taylor The tautomerism of 1,2,3-triazole in aqueous solution Journal of the Chemical Society, Perkin Transactions 2 11 1903–1905 1989 10.1039/P29890001903 It is a surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms. However, flash vacuum pyrolysis at 500 °C leads to loss of molecular nitrogen (N2) leaving a three-member aziridine ring. Certain triazoles are relatively easy to cleave due to ring–chain tautomerism. One manifestation is found in the Dimroth rearrangement. Applications 1,2,3-Triazole finds use in research as a bioisostere for imidazoles and various carboxylic acid derivatives in medicinal chemistry.Bonandi, E. Christodoulou, M. S. Fumagalli, G. Perdicchia, D. Rastelli, G. Passarella, D. The 1,2,3-triazole ring as a bioisostere in medicinal chemistry Drug Discov Today 2017 22 10 1572–1581 28676407 10.1016/j.drudis.2017.05.014 11380/1153568 free Consequently it is an industrial building block for more complex chemicals, including pharmaceutical drugs such as mubritinib and tazobactam. References Category:Triazoles Category:Organic compounds with 2 carbon atoms