Simple and efficient one-pot synthesis of 2,4-diaryl-1,2,3-triazoles

Synthetic Communications

Volumn 36, Issue 17, 2006, Pages 2461-2468

  Tang, Wen Jie ^a   Hu, Yong Zhou ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

2,4,5 triaryl 1,2,3 triazoles; 2,4 Diaryl 1,2,3 triazoles; Synthesis

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 2,4 DIPHENYL 1,2,3 TRIAZOLE DERIVATIVE; PHENYLHYDRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS;

EID: 33748476654     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600781216     Document Type: Article

References (23)

1. Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl) oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem. 2000, 43, 953.
2. Machin, P. J.; Hurst, D. N.; Bradshaw, R. M.; Blaber, L. C.; Burden, D. T.; Melarange, R. A. Beta 1-selective adrenoceptor antagonists, 3: 4-Azolyl-linked phenoxypropanolamines. J. Med. Chem. 1984, 27, 503.
3. Velazquez, S.; Alvarez, R.; Perez, C.; Gago, F.; De-Clercq, D.; Balzarini, Camarasa M. Regiospecific synthesis and anti-human immunodeficiency virus activity of novel 5-substituted N-alkylcarbamoyl and N,N-dialkylcarbamoyl 1,2,3-triazole-TSAO analogues. J. Antivir. Chem. Chemother. 1998, 9, 481.
4. Biagi, G.; Calderone, V.; Giorgi, I.; Livi, O.; Scartoni, V.; Baragatti, B.; Martinotti, E. 5-(4′-Substituted-2′-nitroanilino)-1,2,3- triazoles as new potential potassium channel activators. I. Eur. J. Med. Chem. 2000, 35, 715.
5. Looker, J. J. Preparation of 1,2,3-triazoles from 7-azido-1,3,5- cycloheptatriene: A displacement from nitrogen. J. Org. Chem. 1965, 30, 638.
6. Howell, S. J.; Spencer, N.; Philp, D. Recognition-mediated regiocontrol of a dipolar cycloaddition reaction. Tetrahedron 2001, 57, 4945.
7. Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Highly efficient and mild synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives. Tetrahedron Lett. 2001, 42, 9117.
8. Peng, W.; Zhu, S. Efficient synthesis of 5-fluoroalkylated 1H-1,2,3-triazoles and application of the bromodifluoromethylated triazole to the synthesis of novel bicyclic gem-difluorinated 1H-pyrano[3,4-d][1,2,3]- triazol-4-one compounds. Tetrahedron 2003, 59, 4395.
9. Elkhadem, H.; Elshafei, Z. M.; Hashem, M. M. Reactions of benzil mono- and bis-arylhydrazones. J. Chem. Soc. C 1968, 949.
10. Elkhadem, H.; Elsadik, M. M.; Meshreki, M. H. Reactions of phenylglyoxal bisarylhydrazones. J. Chem. Soc. C 1968, 2097.
11. Balachandran, K. S.; Hiryakkanavar, I.; George, M. V. Oxidation with metal oxides, VIII: Oxidation of bisphenylhydrazones of 1,2-diketones with nickel peroxide. Tetrahedron 1975, 31, 1171.
12. Elkhadem, H.; Elshaefi, Z. M. The scope and mechanism of carbohydrate osotriazole formation, part II: The action of oxidising agents on osazones and osotriazoles. J. Chem. Soc. 1958, 3117.
13. Bhatnagar, I.; George, M. V. Oxidation of phenylhydrazones with manganese dioxide. J. Org. Chem. 1967, 32, 2252.
14. Latif, N.; Meguid, S. A. Cabonyl and thiocarbonyl compounds, part XIII: 2-Aroyl-1,3-benzo-dioxoles of potential pesticidal activity and their cleavage with hydrazines. J. Chem. Soc., Perkin Trans. 1 1972, 1095.
15. Wintner, C. Photocyclization of bisphenylazostilbene: An apparent new source of phenyl imidogen [phenyl nitrene]. Tetrahedron Lett. 1970, 26, 2275.
16. Hansruedi, M.; Heinzelmann, W.; Heinz, H. Direct detection of diphenylnitrilimine in the photolysis of 2,5-diphenyltetrazole. Chimia 1980, 34, 504.
17. Xu, B. H.; Hu, Y. Z. A facile synthesis of 2-methyl-1,2,3-triazoles. J. Chem. Res., Synop. 2003, 96.
18. Luo, Y.; Hu, Y. Z. A novel and efficient strategy for the preparation of 2,4-disubstituted-1,2,3-triazoles. Synth. Commun. 2003, 33, 3513.
19. Pirkle, W. H.; Simmons, K. A. Improved chiral derivatizing agents for the chromatographic resolution of racemic primary amines. J. Org. Chem. 1983, 48, 2520.
20. Hutchins, R. O.; Taffer, I. M. Aqueous polar aprotic solvents: Efficient sources of nucleophilic oxygen. J. Org. Chem. 1983, 48, 1360.
21. Moderhack, D.; Daoud, H. 1,2,3- And 1,2,4-triazolium salts, pyrazoles, and quinoxalines from diaryl nitrilimines and isocyanides: A study of the scope. J. Heterocycl. Chem. 2003, 40, 625.
22. Hann, R. M.; Hudson, C. S. Action of Cu sulfate on phenylosazones of the sugars: Phenyl-D-glucosotriazole. J. Am. Chem. Soc. 1944, 66, 735.
23. Sukumaran, K. B.; Angadiyavar, C. S.; George, M. V. 1,3-Dipolar cycloadditions of anhydro-1-phenylimino-2,4,5-triphenyl-1,2,3-triazolium hydroxide. Tetrahedron 1972, 28, 3987.