Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

Organic Letters

Volumn 17, Issue 12, 2015, Pages 2898-2901

  Bai, Hui Wen ^a   Cai, Zhong Jian ^a   Wang, Shun Yi ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYDRAZONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TRIAZOLE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

AMINES; CYCLIZATION; HYDRAZONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; TOSYL COMPOUNDS; TRIAZOLES;

EID: 84935016063     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01000     Document Type: Article

References (44)

1. Wamhoff, H. In Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; p 669.
2. Abu-Orabi, S. T.; Atfah, M. A.; Jibril, I.; MariI, F. M.; Ali, A. A. J. Heterocycl. Chem. 1989, 26, 1461-1468
3. Fan, W.-Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II, Vol. 4; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; p 1-126.
4. Alvarez, R.; Velazquez, S.; San, F.; Aquaro, S.; De, C.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185-4181
5. Baures, P. W. Org. Lett. 1999, 1, 249-252
6. Palmer, L. M.; Janson, C. A.; Smith, W. W. PCT Int. Appl. 2005; p 347. CODEN: PIXXD2 WO 2005016237 A2 20050224, CAN: 142:256748 (patent written in English).
7. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598
8. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633-645
9. Huisgen, R.; Knorr, R.; Möbius, L.; Szeimies, G. Chem. Ber. 1965, 98, 4014-4021
10. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. 2002, 114, 2708-2711
11. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
12. Tornøe, C. W.; C. Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
13. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
14. Zhang, L.; Chen, X. G.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998-15999
15. Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337-5339
16. Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923-8930
17. Johansson, J. R.; Lincoln, P.; Norden, B.; Kann, N. J. Org. Chem. 2011, 76, 2355-2359
18. For Sm(III)-catalyzed azide-alkyne cycloaddition, see: Hong, L.; Lin, W.; Zhang, F.; Liu, R.; Zhou, X. Chem. Commun. 2013, 49, 5589-5591
19. Ding, S.; Jia, G.; Sun, J. Angew. Chem., Int. Ed. 2014, 53, 1877-1880
20. Barluenga, J.; Valdés, C.; Beltrán, G.; Escribano, M.; Aznar, F. Angew. Chem., Int. Ed. 2006, 45, 6893-6896
21. Wang, Y. C.; Xie, Y. Y.; Qu, H. E.; Wang, H. S.; Pan, Y. M.; Huang, F. P. J. Org. Chem. 2014, 79, 4463-4469
22. Brunner, M.; Maas, G.; Klarner, F.-G. Helv. Chim. Acta 2005, 88, 1813-1825
23. Belkheira, M.; El Abed, D.; Pons, J.-M.; Bressy, C. Chem.-Eur. J. 2011, 17, 12917-12921
24. Danence, L. J. T.; Gao, Y.; Li, M.; Huang, Y.; Wang, J. Chem.-Eur. J. 2011, 17, 3584-3587
25. Seus, N.; Goncalves, L. C.; Deobald, A. M.; Savegnago, L.; Alves, D.; Paixao, M. W. Tetrahedron. 2012, 68, 10456-10463
26. Wang, L.; Peng, S.; Danence, L. J. T.; Gao, Y.; Wang, J. Chem.-Eur. J. 2012, 18, 6088-6093
27. Li, W.; Jia, Q.; Du, Z.; Wang, J. Chem. Commun. 2013, 49, 10187-10189
28. Cheng, G.; Zeng, X.; Shen, J.; Wang, X.; Cui, X. Angew. Chem., Int. Ed. 2013, 52, 13265-13268
29. Thomas, J.; John, J.; Parekh, N.; Dehaen, W. Angew. Chem., Int. Ed. 2013, 53, 10155-10159
30. Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2014, 16, 5728-5731
31. Chen, Z. K.; Yan, Q. Q.; Liu, Z. X.; Xu, Y. M.; Zhang, Y. H. Angew. Chem., Int. Ed. 2013, 52, 13324-13328
32. Chen, Z.; Yan, Q.; Yi, H.; Liu, Z.; Lei, A.; Zhang, Y. Chem.-Eur. J. 2014, 20, 13692-13697
33. van Berkel, S. S.; Brauch, S.; Gabriel, L.; Henze, M.; Stark, S.; Vasilev, D.; Wessjohann, L. A.; Abbas, M.; Westermann, B. Angew. Chem., Int. Ed. 2012, 51, 5343-5346
34. Sakai, K.; Hida, N.; Kondo, K. Bull. Chem. Soc. Jpn. 1986, 59, 179-183
35. Ramasastry, S. S. V. Angew. Chem., Int. Ed. 2014, 53, 14310-14312
36. Cai, Z.-J.; Lu, X.-M.; Zi, Y.; Yang, C.; Shen, L.-J.; Li, J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2014, 16, 5108-5111
37. Attanasi, O. A.; De Crescentini, L.; Favi, G.; Filippone, P.; Mantellini, F.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2009, 3109-3112
38. Rossi, E.; Arcadi, A.; Abbiati, G.; Attanasi, O. A.; Crescentini, L. D. Angew. Chem., Int. Ed. 2002, 41, 1400-1402
39. Attanasi, O. A.; Favi, G.; Filippone, P.; Giorgi, G.; Mantellini, F.; Moscatelli, G.; Spinelli, D. Org. Lett. 2008, 10, 1983-1986
40. Attanasi, O. A.; Favi, G.; Filippone, P.; Mantellini, F.; Moscatelli, D.; Perrulli, F. R. Org. Lett. 2010, 12, 468-471
41. Attanasi, O. A.; Favi, G.; Mantellini, F.; Moscatelli, G.; Santeusanio, S. Adv. Synth. Catal. 2011, 353, 1519-1524
42. Chen, J.-R.; Dong, W.-R.; Candy, M.; Pan, F.-F.; Jörres, M.; Bolm, C. J. Am. Chem. Soc. 2012, 134, 6924-6927
43. Hatcher, J. M.; Coltart, D. M. J. Am. Chem. Soc. 2010, 132, 4546-4547
44. Tong, M.-C.; Chen, X.; Li, J.; Huang, R.; Tao, H.; Wang, C.-J. Angew. Chem., Int. Ed. 2014, 53, 4680-4684