Multicomponent synthesis of 1-aryl 1,2,4-triazoles

Organic Letters

Volumn 15, Issue 14, 2013, Pages 3586-3589

  Tam, Annie ^a   Armstrong, Ian S ^a   La Cruz, Thomas E ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE; 1,2,4-TRIAZOLE; ANILINE DERIVATIVE; HETEROCYCLIC COMPOUND; PYRIMIDINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANILINE COMPOUNDS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; PYRIMIDINES; TRIAZOLES;

EID: 84880538099     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401428x     Document Type: Article

References (30)

1. Al-Masoudi, A.; Al-Soud, Y. A.; Al-Salihi, N. J.; Al-Masoudi, N. A. Chem. Heterocycl. Compd. 2006, 42, 1377-1403
2. Pibiri, I.; Buscemi, S. Current Bioactive Compounds 2010, 6, 208-242
3. Sahoo, S.; Veliyath, S. K.; Mahendra Kumar, C. B. Int. J. Res. Pharm. Sci. 2012, 3, 326-333
4. Shalini, K.; Kumar, N.; Drabu, S.; Sharma, P. K.; Beilstein J. Org. Chem. 2011, 7, 668-677
5. Naik, A. D.; Diîrtu, M. M.; Railliet, A. P.; Marchand-Brynaert, J.; Garcia, Y. Polymer 2011, 3, 1750-1775
6. Klingele, M. H.; Brooker, S. Coord. Chem. Rev. 2003, 241, 119-132
7. Haasnoot, J. G. Coord. Chem. Rev. 2000, 200-202, 131-185 and references therein
8. Moulin, A.; Bibian, M.; Blayo, A.-L.; El Habnouni, S.; Martinez, J.; Fehrentz, J.-A. Chem. Rev. 2010, 110, 1809-1827
9. Yet, L. Prog. Heterocycl. Chem. 2011, 23, 231-266
10. Curtis, A. D. M. Sci. Synth. 2004, 13, 603-639
11. Holm, S. C.; Straub, B. F. Org. Prep. Proc. Int. 2011, 43, 319-347
12. Staben, S. T.; Blaquiere, N. Angew. Chem., Int. Ed. 2010, 49, 325-328
13. Castanedo, G. M.; Seng, P. S.; Blaquiere, N.; Trapp, S.; Staben, S. T. J. Org. Chem. 2011, 76, 1177-1179
14. An elegant copper catalyzed approach to 1,2,4-triazoles: Xu, H.; Jiang, Y.; Fu, H. Synlett 2013, 24, 125-129
15. Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063-5073 and references therein
16. Terauchi, J.; Koike, T.; Honda, E.; Nakamura, M.; Kajita, Y.; Hoashi, Y.; Morimoto, S.; Fujimoto, T. Preparation of Piperazines and Related Compounds for Inhibiting Amyloid-β Production. PCT Int. Appl., 2011002067.
17. For an example of C-N coupling metal-mediated synthesis of fused 1,2,4-triazoles from amino pyridines, see: Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080-15081
18. Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578-5587
19. Yang, K.; Qiu, Y.; Zheng, Li, Z.; Wang, Z.; Jiang, S. J. Org. Chem. 2011, 76, 3151-3159
20. Albrecht, B. K.; Gehling, V. S.; Hewitt, M. C.; Taylor, A. M.; Harmange, J.-C. Preparation of 4H-Benzo[b][1,2,4]Triazolo[4,3-d][1,4]Diazepine Derivatives as Bromodomain Inhibitors. PCT Int. Appl., 2012151512.
21. Aspnes, G. E.; Didiuk, M. T.; Filipski, K. J.; Guzman-Perez, A.; Lee, E. C. Y.; Pfefferkorn, J. A.; Stevens, B. D.; Tu, M. M. Preparation of 3-[4-(Heterocyclyl-Substituted)-Benzamido]Propanoic Acids as Glucagon Receptor Modulators. U.S. Pat. Appl., 20120202834.
22. De Cleyn, M. A. J.; Van Brandt, S. F. A.; Gijsen, H. J. M.; Berthelot, D. J-C.; Oehlrich, D. Triazole Derivatives as Gamma-Secretase Modulators and Their Preparation and Use for the Treatment of Diseases. PCT Int. Appl. WO 2011086098 A1.
23. Kamenecka, T. M.; Jiang, R.; Song, X.; Lograsso, P.; Cameron, M. D. Preparation of Phenylaminopyrimidine Derivatives and Analogs as Protein Kinase Inhibitors. PCT Int. Appl. WO 2009032861.
24. Naidu, B. N.; Connolly, T. P.; Ueda, Y. Cyclic Pyrimidinone Derivatives as HIV Integrase Inhibitors and Their Preparation, Pharmaceutical Compositions and Use in the Treatment of HIV Infections. U.S. Patent, 7419969.
25. For a discussion on the regioselectivity of 1,2,4-triazole alkylation: Bulger, P. G.; Cottrell, I. F.; Cowden, C. J.; Davies, A. J.; Dolling, U.-H. Tetrahedron Lett. 2000, 41, 1297-1301
26. Roberts, R. M. J. Am. Chem. Soc. 1949, 71, 3848-3849 and references therein
27. Preparation of tosyl amidoxime 5: Inagaki, T.; Kurita, Y.; Hirakata, K.; Mizutani, A.; Kondo, M. Preparation of Alkoximino-5-Amino-1,2,4-thiadiazole-3- Acetates. Eur. Pat. Appl. EP 0795551 A1.
28. For a review on the structure and chemistry of hydroxylamidoximes, see: Katritzky, A. R.; Huang, L.; Chahar, M.; Sakhuja, R.; Hall, C. D. Chem. Rev. 2012, 112, 1633-1649
29. For an example illustrating a N-N bond forming cyclization reaction using a mesylated oxime, see: Wray, B. C.; Stambuli, J. P. Org. Lett. 2010, 12, 4576-4579
30. Roberts, R. M.; DeWolfe, R. H. J. Am. Chem. Soc. 1954, 76, 2411-2414 and references therein