An efficient and clean CuI-catalyzed chalcogenylation of aromatic azaheterocycles with dichalcogenides

Tetrahedron

Volumn 67, Issue 20, 2011, Pages 3690-3697

  Li, Zhen ^a   Hong, Jianquan ^a   Zhou, Xigeng ^a,b  

^a FUDAN UNIVERSITY   (China)

^b Laboratory of Organometallic Chemistry Shanghai   (China)

Author keywords

Air; Azaheterocycles; Chalcogenylation; Copper(I) iodide; Dichalcogenides

Indexed keywords

CHALCOGEN; COPPER ION; DICHALCOGENIDE DERIVATIVE; IMIDAZOPYRIDINE DERIVATIVE; IMIDAZOPYRIMIDINE DERIVATIVE; INDOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLO[2,3 B]PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PRIORITY JOURNAL;

EID: 79955523291     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.067     Document Type: Article

References (57)

1. T.M. Williams, T.M. Ciccarone, S.C. MacTough, C.S. Rooney, S.K. Balani, J.H. Condra, E.A. Emini, M.E. Goldman, W.J. Greenlee, L.R. Kauffman, J.A. O'Brien, V.V. Sardana, W.A. Schleif, A.D. Theoharides, and P.S. Anderson J. Med. Chem. 36 1993 1291
2. M. Raban, and L. Chern J. Org. Chem. 45 1980 1688
3. P.F. Ranken, and B.G. McKinnie J. Org. Chem. 54 1989 2985
4. C.C. Browder, M.O. Mitchell, R.L. Smith, and G. el-Sulayman Tetrahedron Lett. 34 1993 6245
5. P. Hamel, and P. Préville J. Org. Chem. 61 1996 1573
6. P. Hamel Tetrahedron Lett. 38 1997 8473
7. P. Hamel J. Org. Chem. 67 2002 2854
8. K.M. Schlosser, A.P. Krasutsky, H.W. Hamilton, J.E. Reed, and K. Sexton Org. Lett. 6 2004 819
9. M. Tudge, M. Tamiya, C. Savarin, and G. Humphrey Org. Lett. 8 2006 565
10. C.,C. Silveira, S.,R. Mendes, L. Wolf, and G.M. Martins Tetrahedron Lett. 51 2010 2014
11. M. Matsugi, K. Murata, K. Gotanda, H. Nambu, G. Anilkumar, K. Matsumoto, and Y. Kita J. Org. Chem. 66 2001 2434
12. Y.J. Guo, R.Y. Tang, J.H. Li, P. Zhong, and X.G. Zhang Adv. Synth. Catal. 351 2009 2615
13. Y. Chen, C.H. Cho, and R.C. Larock Org. Lett. 11 2009 173
14. P.C. Montevecchi, M.L. Navacchia, and P. Spagnolo Eur. J. Org. Chem. 6 1998 1219
15. P. Barraja, P. Diana, A. Carbone, and G. Cirrincione Tetrahedron 64 2008 11625
16. R. Sanz, V. Guilarte, and M.P. Castroviejo Synlett 2008 3006
17. J.S. Yadav, B.V.S. Reddy, and Y.J. Reddy Tetrahedron Lett. 48 2007 7034
18. J.S. Yadav, B.S. Reddy, Y.J. Reddy, and K. Praneeth Synthesis 9 2009 1520
19. Y. Maeda, M. Koyabu, and T. Nishimura J. Org. Chem. 69 2004 7688
20. X.L. Fang, R.Y. Tang, P. Zhong, and J.H. Li Synthesis 24 2009 4183
21. S. Fukuzawa, E. Shimizu, Y. Atsuumi, M. Haga, and K. Ogata Tetrahedron Lett. 50 2009 2374
22. For selected recent examples on biological 2-azole thioethers:
23. M.D. Berger, M. Dutia, D. Powell, B.M. Floyd, N. Torres, R. Mallon, D. Wojciechowicz, S. Kim, L. Feldberg, K. Collins, and I. Chaudhary Bioorg. Med. Chem. 16 2008 9202
24. M. Hayakawa, H. Kaizawa, K. Kawaguchi, N. Ishikawa, T. Koizumi, T. Ohishi, M. Yamano, M. Okada, M. Ohta, S. Tsukamoto, F.I. Raynaud, M.D. Waterfield, P. Parker, and P. Workman Bioorg. Med. Chem. 15 2007 403
25. Y.G. Gu, M. Weitzberg, R.K. Clark, X. Xu, Q. Li, T. Zhang, T.M. Hansen, G. Liu, Z. Xin, X. Wang, R. Wang, T. McNally, H. Camp, B.A. Beutel, and H.L. Sham J. Med. Chem. 49 2006 3770
26. V.K. Tandon, D.B. Yadav, R.V. Singh, A.K. Chaturvedi, and P.K. Shukla Bioorg. Med. Chem. Lett. 15 2005 5324
27. L. Llauger, H. He, J. Kim, J. Aguirre, N. Rosen, U. Peters, P. Davies, and G. Chiosis J. Med. Chem. 48 2005 2892
28. For selected recent examples on medicinal 3-sulfenyl indoles:
29. R. Silvestri, G. De Martino, G. La Regina, M. Ártico, S. Massa, L. Vargiu, M. Mura, A.G. Loi, T. Marceddu, and P. La Colla J. Med. Chem. 46 2003 2482
30. I. Avis, A. Martinez, J. Tauler, E. Zudaine, A. Mayburd, R. Abu-Ghazaleh, F. Obndrey, and J.L. Mulshine Cancer Res. 65 2005 4181
31. C.D. Funk Nat. Rev. Drug Discovery 4 2005 664
32. G. De Martino, G. La Regina, A. Coluccia, M.C. Edler, M.C. Barbera, A. Brancale, E. Wilcox, E. Hamel, M. Artico, and R. Silvestri J. Med. Chem. 47 2004 6120
33. G. De Martino, M.C. Edler, G. La Regina, A. Coluccia, M.C. Barbera, D. Barrow, R.I. Nicholson, G. Chiosis, A. Brancale, E. Hamel, M. Artico, and R. Silvestri J. Med. Chem. 49 2006 947
34. D.P. Becker, D.L. Flynn, A.E. Moormann, R. Nosal, C.I. Villamil, R. Loeffler, G.W. Gullikson, C. Moummi, and D.C. Yang J. Med. Chem. 49 2006 1125
35. R. Abou-Jneid, S. Ghoulami, M.T. Martin, E.T.H. Dau, N. Travert, and A. Al-Mourabit Org. Lett. 6 2004 3933
36. A.N. Jain J. Med. Chem. 47 2004 947
37. N.K. Hart, S.R. Johns, and J.A. Lamberton J. Chem. Soc., Chem. Commun. 1969 484
38. S.M. Hanson, E.V. Morlock, K.A. Satyshur, and C. Czajkowski J. Med. Chem. 51 2008 7243
39. H.Z. Si, N. Lian, S.P. Yuan, A.P. Fu, Y.B. Duan, K.J. Zhang, and X.J. Yao Eur. J. Med. Chem. 44 2009 4044
40. C. Mustazza, G. Del, R. Maria, A. Borioni, and F. Gatta J. Heterocycl. Chem. 38 2001 1119
41. A.,C. Humphries, E. Gancia, M.T. Gilligan, S. Goodacre, D. Hallett, K.J. Merchant, and S.R. Thomas Bioorg. Med. Chem. Lett. 16 2006 1518
42. F. Juan, S. Violeta, L. Carmen, A.C. José, M. Antonio, M.C. José, and C.T. Athanassios Organometallics 29 2010 1396
43. C. Hamdouchi, J.D. Blas, and J. Ezquerra Tetrahedron 55 1999 541
44. W. Huang, Q.S. Shen, J.L. Wang, and X.G. Zhou J. Org. Chem. 73 2008 1586
45. W. Huang, P.Z. Zheng, Z.X. Zhang, R.T. Liu, Z.X. Chen, and X.G. Zhou J. Org. Chem. 73 2008 6845
46. W. Huang, L.C. Hong, P.Z. Zheng, R.T. Liu, and X.G. Zhou Tetrahedron 65 2009 3603
47. J.L. Wang, L.X. Zhang, Y.F. Jing, W. Huang, and X.G. Zhou Tetrahedron Lett. 50 2009 4978
48. A. Stein, D. Alves, J. da Rocha, C. Nogueira, and G. Zeni Org. Lett. 10 2008 4983
49. N. Taniguchi J. Org. Chem. 71 2006 7874
50. N. Taniguchi Tetrahedron 65 2009 2782
51. H. Takeuchi, T. Hiyama, N. Kamai, and H. Oya J. Chem. Soc., Perkin Trans. 2 1997 2301
52. N. Taniguchi Synlett 2006 1351
53. S. Takizawa, J. Nishida, T. Tsuzuki, S. Tokito, and Y. Yamashita Inorg. Chem. 46 2007 4308
54. G.W. Kabalka, M.S. Reddy, and M.L. Yao Tetrahedron Lett. 50 2009 7340
55. M.H. Ali, and M. McDermott Tetrahedron Lett. 43 2002 6271
56. S. Roy, A. Eastman, and G.W. Gribble Tetrahedron 62 2006 7838
57. CCDC 784894, 784895 for 3ae and 5ha contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif.