Facile route for N1-aryl benzotriazoles from diazoamino arynes via CuI-mediated intramolecular N-arylation

Tetrahedron Letters

Volumn 51, Issue 43, 2010, Pages 5740-5743

  Kale, Raju R ^a   Prasad, Virendra ^a   Hussain, H A ^a   Tiwari, Vinod K ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

Amines; Benzotriazole; CuI; Diazonium salt; N Arylation

Indexed keywords

2 CHLORO 1,2,3 BENZOTRIAZENE; BENZOTRIAZOLE DERIVATIVE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; SYNTHESIS;

EID: 77957140633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.083     Document Type: Article

References (34)

1. R. Carlini, E. Bria, D. Giannarelli, G. Ferretti, A. Felici, P. Papaldo, A. Fabi, C. Nistico, and S. Cosimo Di.; Ruggeri, E. M.; Milella, M.; Mottolese, M.; Terzoli, E.; Cognetti, F. Cancer 104 2005 1335 1557
2. G. Semple, P.J. Skinner, M.C. Cherrier, P.J. Webb, C.R. Sage, S.Y. Tamura, R. Chen, J.G. Richman, and D.T. Connolly J. Med. Chem. 49 2006 1227 1230
3. A.J. Dipesa, K.M. Donahue, M.A. Dombroski, N.C. Elliott, C.A. Gabel, S. Han, T.R. Hynes, P.K. LeMotte, M.N. Mansour, E.S. Marr, M.A. Letavic, J. Pandit, D.B. Ripin, F.J. Sweeney, D. Tan, and Y. Tao J. Med. Chem. 48 2005 5728 5737
4. C.Y. Wu, K.Y. King, J.M. Fang, Y.T. Wu, M.Y. Ho, C.L. Liao, J. Shie, P.H. Liang, and C.H. Wong Chem. Biol. 13 2006 261 268
5. A.R. Katritzky, J. Jiang, and L. Urogdi Tetrahedron Lett. 25 1989 3303 3306
6. P.A. Wender, S.M. Touami, C. Alayrac, and U.C. Philipp J. Am. Chem. Soc. 118 1996 6522 6523
7. G. Caliendo, G. Greco, P. Grieco, E. Novellino, E. Perissuttil, V. Santagada, D. Barbarul, E. Esposit, and A. De Blas Eur. J. Med. Chem. 31 1996 207 213
8. A.R. Katritzky, X. Lan, Z. Jason, Z. Yang, and O.V. Denisko Chem. Rev. 98 1998 409 548
9. A.R. Katritzky, K. Manju, S.K. Singh, and N.K. Meher Tetrahedron 61 2005 2555 2581
10. A.R. Katritzky, and B.V. Rogovoy Chem. Eur. J. 19 2003 4586 4593
11. A.R. Katritzky, and X. Lan Chem. Soc. Rev. 23 1994 363 373
12. A.R. Katritzky, S.A. Henderson, and B. Yang J. Heterocycl. Chem. 35 1998 1123 1159
13. A.K. Verma, T. Kesharwani, J. Singh, V. Tandon, and R.C. Larock Angew. Chem., Int. Ed. 48 2009 1138 1143
14. R.R. Kale, V. Prasad, P.P. Mohapatra, and V.K. Tiwari Monatsh. Chem. 2010 10.1007/s00706-010-0378-1
15. G.A. Reynolds J. Org. Chem. 29 1964 3733 3734
16. B. Karine, D.M. Adam, and E.M. John Org. Lett. 9 2007 1809 1811
17. F. Zhang, and J.E. Moses Org. Lett. 11 2009 1587 1590
18. F. Shi, J.P. Waldo, Y. Chen, and R.C. Larock Org. Lett. 10 2008 2409 2412
19. S. Chandrasekhar, M. Seenaiah, C.L. Rao, and C.R. Reddy Tetrahedron 64 2008 11325 11327
20. L. Campbell-Verduyn, P.H. Elsinga, L. Mirfeizi, R.A. Dierckx, and B.L. Feringa Org. Biomol. Chem. 6 2008 3461 3463
21. T. Kitamura, N. Fukatsu, and Y. Fujiwara J. Org. Chem. 63 1998 8579 8581
22. V. Zimmermann, and S. Brase J. Comb. Chem. 9 2007 1114 1137
23. C.M.P. Pereira, H.A. Stefani, K.P. Guzenc, and A.T.G. Orfaoa Lett. Org. Chem. 4 2007 43 46
24. P. Sanna, A. Carta, and G. Paglietti Heterocycles 50 1999 693 702
25. A. Carta, G. Boatto, G. Paglietti, G. Poni, M.G. Setzu, and P. Caredda Heterocycles 60 2003 833 842
26. P. Corona, S. Piras, M. Palomba, and A. Carta Mini-Rev. Org. Chem. 5 2008 295 302
27. R.R. Kale, V. Prasad, and V.K. Tiwari Lett. Org. Chem. 7 2010 136 143
28. V.K. Tiwari, A. Singh, H.A. Hussain, B.B. Mishra, and V. Tripathi Monatsh. Chem. 138 2007 1297 1302
29. V.K. Tiwari, H.A. Hussain, B.B. Mishra, D.D. Singh, and V. Tripathi Med. Chem. Res. 15 2007 325 327
30. A. Singh, R.R. Kale, and V.K. Tiwari Trends Carbo. Res. 1 2009 80 85
31. V.K. Tiwari, D.D. Singh, H.A. Hussain, B.B. Mishra, and A. Singh Monatsh. Chem. 139 2008 43 48
32. Q. Ding, X. He, and J. Wu J. Comb. Chem. 11 2009 587 591
33. V. Prasad, R.R. Kale, B.B. Mishra, and V.K. Tiwari Trends Carbohydrate Res. 1 2009 43 49
34. 3, 75 MHz): δ 142.8, 139.6, 133.7, 133.5, 132.8, 130.2, 129.8, 128.8, 128.2, 127.0, 126.4, 125.6, 124.4, 121.7, 118.4, 116.5 ppm.