Synthesis and Z/E isomerization of 2-imino-1,3-thiaselenolanes via iodocyclization

Tetrahedron

Volumn 68, Issue 51, 2012, Pages 10496-10501

  Toyoda, Yosuke ^a,b   Koketsu, Mamoru ^a  

^a GIFU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; IMINE; ISOCYANIC ACID DERIVATIVE; SELENIUM DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONJUGATION; CYCLIZATION; IODOCYCLIZATION; ISOMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84868464269     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.07.083     Document Type: Article

References (52)

1. T. Imakubo, T. Shirahata, and M. Kibune Chem. Commun. 2004 1590 1591
2. T. Shirahata, M. Kibune, H. Yoshino, and T. Imakubo Chem. - Eur. J. 13 2007 7619 7630
3. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, and R.J.K. Taylor Comprehensive Heterocyclic Chemistry III. A Review of the Literature 1995-2007 Vol. 2 2008 Elsevier Science Oxford pp 463-477
4. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, and R.J.K. Taylor Comprehensive Heterocyclic Chemistry III. A Review of the Literature 1995-2007 Vol. 4 2008 Elsevier Science Oxford pp 755-821
5. D.M. Freudendahl, S.A. Shahzad, and T. Wirth Eur. J. Org. Chem. 2009 1649 1664
6. G. Mugesh, W.W. du Mont, and H. Sies Chem. Rev. 101 2001 2125 2179
7. T.G. Back, and Z. Moussa J. Am. Chem. Soc. 125 2003 13455 13460
8. C.W. Nogueira, G. Zeni, and J.B.T. Rocha Chem. Rev. 104 2004 6255 6285
9. M. Ninomiya, D.R. Garud, and M. Koketsu Coord. Chem. Rev. 255 2011 2968 2990
10. D.R. Garud, M. Koketsu, and H. Ishihara Molecules 12 2007 504 535
11. H. Heimgartner, Y. Zhou, P.K. Atanassov, and G.L. Sommen Phosphorus, Sulfur Silicon Relat. Elem. 183 2008 840 855
12. M. Ninomiya, D.R. Garud, and M. Koketsu Heterocycles 81 2010 2027 2055
13. G.L. Sommen, A. Linden, and H. Heimgartner Eur. J. Org. Chem. 2005 3128 3137
14. G.L. Sommen, A. Linden, and H. Heimgartner Tetrahedron Lett. 46 2005 6723 6725
15. Y. Toyoda, D.R. Garud, and M. Koketsu Heterocycles 78 2009 449 456
16. D.R. Garud, Y. Toyoda, and M. Koketsu Tetrahedron Lett. 50 2009 3035 3037
17. M. Frederickson, and R. Grigg Org. Prep. Proced. Int. 29 1997 33 62
18. F.M. da Silva, J. Jones, and M.C.S. de Mattos Curr. Org. Synth. 2 2005 393 414
19. M.J. Mphahlele Molecules 14 2009 4814 4837
20. P.T. Parvatkar, P.S. Parameswaran, and S.G. Tilve Chem. - Eur. J. 18 2012 5460 5489
21. M. Koketsu, T. Kiyokuni, T. Sakai, H. Ando, and H. Ishihara Chem. Lett. 35 2006 626 627
22. D.R. Garud, and M. Koketsu Org. Lett. 10 2008 3319 3322
23. D.R. Garud, M. Makimura, H. Ando, H. Ishihara, and M. Koketsu Tetrahedron Lett. 48 2007 7764 7768
24. A.Z. Halimehjani, H. Maleki, and M.R. Saidi Tetrahedron Lett. 50 2009 2747 2749
25. S.V. Amosova, M.V. Penzik, V.A. Potapov, and A.I. Albanov Russ. Chem. Bull. 57 2008 1323
26. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov Russ. J. Gen. Chem. 79 2009 161
27. V.A. Potapov, K.A. Volkova, and S.V. Amosova Russ. J. Gen. Chem. 79 2009 1758 1759
28. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov Tetrahedron Lett. 50 2009 306 308
29. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov J. Organomet. Chem. 694 2009 3369 3372
30. V.A. Potapov, E.O. Kurkutov, and S.V. Amosova Russ. J. Gen. Chem. 80 2010 1220 1221
31. V.A. Potapov, E.O. Kurkutov, M.V. Musalov, and S.V. Amosova Tetrahedron Lett. 51 2010 5258 5261
32. V.A. Potapov, V.A. Shagun, M.V. Penzik, and S.V. Amosova J. Organomet. Chem. 695 2010 1603 1608
33. V.A. Potapov, E.O. Kurkutov, S.V. Amosova, and Y.Y. Rusakov Russ. Chem. Bull. 60 2011 196 197
34. J.G. Fernandez-Bolanos, O. Lopez, V. Ulgar, I. Maya, and J. Fuentes Tetrahedron Lett. 45 2004 4081 4084
35. A. Shafiee, and G. Fanaii Synthesis 1984 512 514
36. N.I. Zmitrovich, M.L. Petrov, and A.A. Petrov Zh. Org. Khim. 26 1990 179 184
37. N.I. Zmitrovich, M.L. Petrov, and A.A. Petrov Zh. Org. Khim. 27 1991 1394 1398
38. G.L. Sommen, A. Linden, and H. Heimgartner Heterocycles 65 2005 1903 1915
39. M. Koketsu, Y. Fukuta, and H. Ishihara J. Org. Chem. 67 2002 1008 1011
40. M. Koketsu, T. Otsuka, and H. Ishihara Phosphorus, Sulfur Silicon Relat. Elem. 179 2004 443 448
41. T. Murai Organoselenium Chemistry T. Wirth, Synthesis and Reactions 2012 Wiley-VCH Weinheim, Germany 257 285
42. Y. Tamaru, S. Kawamura, and Z. Yoshida Tetrahedron Lett. 26 1985 2885 2888
43. I.V. Alabugin, and T.A. Zeidan J. Am. Chem. Soc. 124 2002 3175 3185
44. I.V. Alabugin, K.M. Gilmore, and P.W. Peterson Wiley Interdiscip. Rev. Comput. Mol. Sci. 1 2011 109 141
45. M. Koketsu, T. Sakai, T. Kiyokuni, D.R. Garud, H. Ando, and H. Ishihara Heterocycles 68 2006 1607 1615
46. H. Sashida, C. Pan, M. Kaname, and M. Minoura Synthesis 2010 3091 3096
47. P.I. Creeke, and J.M. Mellor Tetrahedron Lett. 30 1989 4435 4438
48. J.M. Mellor, and S. Mohammed Tetrahedron Lett. 32 1991 7111 7114
49. Y. Asanuma, S. Fujiwara, T. Shinike, and N. Kambe J. Org. Chem. 69 2004 4845 4848
50. G.L. Sommen, and H. Heimgartner Pol. J. Chem. 81 2007 1413 1418
51. Toyoda, Y.; Ninomiya, M.; Ebihara, M.; Koketsu, M. unpublished data.
52. I. Yavari, and S. Beheshti Helv. Chim. Acta 94 2011 831 834