Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine

Tetrahedron Letters

Volumn 55, Issue 5, 2014, Pages 1082-1085

  Matsumoto, Shoji ^a   Takada, Daiki ^a   Kageyama, Hirokazu ^a   Akazome, Motohiro ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Cyclization reaction; Iodine; Thioamide; Triple bond

Indexed keywords

2 ALKYNYLBENZOTHIOAMIDE; BENZO[C]THIOPHEN 1 AMINIUM IODIDE; BENZOTHIOPHENE DERIVATIVE; IODIDE; IODINE; SOLVENT; THIOAMIDE; THIOBENZAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; X RAY ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 84892787861     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.094     Document Type: Article

References (39)

1. B. Godoi, R.F. Schumacher, and G. Zeni Chem. Rev. 111 2011 2537 2980
2. A.K. Banerjee, M.S. Laya, and E.V. Cabrera Curr. Org. Chem. 15 2011 1058 1080
3. Y. Yamamoto, I.D. Gridnev, N.T. Patil, and T. Jin Chem. Commun. 2009 5075 5087
4. G. Rousseau, and F. Homsi Chem. Soc. Rev. 26 1997 453 461
5. S. Ranganathan, K.M. Muraleedharan, N.K. Vaish, and N. Jayaraman Tetrahedron 60 2004 5273 5308
6. G. Cardillo, and M. Orena Tetrahedron 46 1990 3321 3408
7. M.D. Dowle, and D.I. Davies Chem. Soc. Rev. 8 1979 171 197
8. S. Knapp Adv. Heterocycl. Nat. Prod. Synth. 3 1996 57 98
9. C.L. Campbell, C. Hassler, S.S. Ko, M.E. Voss, M.A. Guaciaro, P.H. Carter, and R.J. Cherney J. Org. Chem. 74 2009 6368 6370
10. T. Hu, K. Liu, M. Shen, X. Yuan, Y. Tang, and C. Li J. Org. Chem. 72 2007 8555 8558
11. S. Ma, and H. Xie Tetrahedron 61 2005 251 258
12. M. Shen, and C. Li J. Org. Chem. 69 2004 7906 7909
13. Q. Ding, Z. Chen, X. Yu, Y. Peng, and J. Wu Tetrahedron Lett. 50 2009 340 342
14. R. Halim, L. Aurelio, P.J. Scammells, and B.L. Flynn J. Org. Chem. 78 2013 4708 4718
15. R. Halim, P.J. Scammells, and B.L. Flynn Org. Lett. 10 2008 1967 1970
16. X. Huang, W. Fu, and M. Miao Tetrahedron Lett. 49 2008 2359 2362
17. I. Aillaud, E. Bossharth, D. Conreaux, P. Desbordes, N. Monteiro, and G. Balme Org. Lett. 8 2006 1113 1116
18. T. Yao, X. Zhang, and R.C. Larock J. Org. Chem. 70 2005 7679 7685
19. Y. Liu, and S. Zhou Org. Lett. 7 2005 4609 4611
20. D. Yue, N.D. Cá, and R.C. Larock J. Org. Chem. 71 2006 3381 3388
21. J. Barluenga, H. Vázquez-Villa, A. Ballesteros, and J.M. González Org. Lett. 5 2003 4121 4123
22. K. Sakthivel, and K. Srinivasan Eur. J. Org. Chem. 2011 2781 2784
23. S. Matsumoto, H. Shibata, and M. Akazome J. Org. Chem. 78 2013 1650 1654
24. D. Chen, G. Song, A. Jia, and X. Li J. Org. Chem. 76 2011 8488 8494
25. T.-S. Jiang, X.-G. Zhang, and J.-H. Li Synthesis 2009 3029 3038
26. K.O. Hessian, and B.L. Flynn Org. Lett. 5 2003 4377 4380
27. D. Yue, and R.C. Larock J. Org. Chem. 67 2002 1905 1909
28. R.C. Larock, and D. Yue Tetrahedron Lett. 42 2001 6011 6013
29. B.L. Flynn, P. Verdier-Pinard, and E. Hamel Org. Lett. 3 2001 651 654
30. H. Sashida, M. Kaname, and M. Minoura Tetrahedron 69 2013 6478 6487
31. A. Tsuneishi, K. Okamoto, Y. Ikeda, M. Murai, K. Miki, and K. Ohe Synlett 2011 655 658
32. G. Ung, M. Soleilhavoup, and G. Bertrand Angew. Chem., Int. Ed. 52 2013 758 761
33. Q. Ding, X. Liu, H. Wang, M. Chen, and Y. Peng Synthesis 44 2012 920 926
34. S. Mehta, T. Yao, and R.C. Larock J. Org. Chem. 77 2012 10938 10944
35. C. Schlemmer, L. Andernach, D. Schollmeyer, B.F. Straub, and T. Opatz J. Org. Chem. 77 2012 10118 10124
36. L. Legrand, and N. Lozac'h Bull. Soc. Chim. Fr. 1966 3828 3841
37. N. Sundaraganesan, and S. Mohan Indian J. Phys. 68B 1994 87 91
38. A.J. Aarts, H.O. Desseyn, B.J. Van der Veken, and M.A. Herman Can. J. Spectrosc. 24 1979 29 34
39. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor J. Chem. Soc., Perkin Trans. 2 1987 S1 S19