Regioselective electrophilic cyclization of o-ethynylbenzyl phenyl selenides to (Z)-1-methylidene-2-phenyl-1,3-dihydro-1H-benzo[c]selenophenium salts

Tetrahedron Letters

Volumn 51, Issue 41, 2010, Pages 5395-5398

  Sashida, Haruki ^a   Nakabayashi, Shoko ^a   Suzuki, Hirokazu ^a   Kaname, Mamoru ^a   Minoura, Mao ^b  

^a HOKURIKU UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLIDENE 2 PHENYL 1,3 DIHYDRO 1H BENZO[C]SELENOPHENIUM; 2 ETHYNYLBENZYLPHENYL SELENIDE DERIVATIVE; SELENIDE; SELENIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROPHILICITY; ROOM TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 78650520670     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.160     Document Type: Article

References (28)

1. This Letter constitutes Part. 32 in the 'Studies on Tellurium-Containing Heterocycles', Part. 31: Sashida, H.; Chao, P.; Kaname, M.; Minoura, M. Synthesis, in press, doi:10.1055/s-0030-1258171. Art ID F07110SS.
2. J. Barluenga, M. Trincado, E. Rubio, and J.M. Gonzalez Angew. Chem., Int. Ed. 42 2003 2406 2409
3. A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, and L. Moro Synlett 1999 1432 1434
4. A. Arcadi, S. Cacchi, S.D. Giuseppe, G. Fabrizi, and F. Marinelli Org. Lett. 4 2002 2409 2412
5. T. Kitamura, T. Takeuchi, H. Kawasato, S. Kobayashi, and H. Taniguchi Tetrahedron Lett. 30 1989 7445 7446
6. T. Kitamura, T. Takeuchi, M. Miyaji, H. Kawasato, and H. Taniguchi J. Chem. Soc., Perkin Trans. 1 1994 1907 1911
7. R.C. Larock, and D. Yue Tetrahedron Lett. 42 2001 6011 6013
8. D. Yue, and R.C. Larock J. Org. Chem. 67 2002 1905 1909
9. B. Flynn, P. Verdier-Pinard, and E. Hamel Org. Lett. 3 2001 651 654
10. A. Matsnev, S. Noritake, Y. Nomura, E. Tokunaga, S. Nakamura, and N. Shibata Angew. Chem., Int. Ed. 49 2010 572 576
11. T. Kesharwani, S.A. Worlikar, and R.C. Larock J. Org. Chem. 71 2006 2307 2312
12. T. Yao, and R.C. Larock Tetrahedron Lett. 43 2002 7401 7404
13. H. Sashida, and K. Ohyanagi J. Chem. Soc., Perkin Trans. 1 1998 2123 2124
14. H. Sashida, and Ohyanagi Heterocycles 51 1999 17 20
15. H. Sashida, K. Ohyanagi, M. Minoura, and K.-y. Akiba J. Chem. Soc., Perkin Trans. 1 2002 606 612
16. Reviews: H. Sashida Rev. Heteroatom Chem. 22 2000 59 78
17. H. Sashida J. Synth. Org. Chem. Jpn. 59 2001 355 362
18. H. Sashida Mini-Rev. Org. Chem. 4 2007 105 114
19. H. Sashida, and M. Minoura J. Synth. Org. Chem. Jpn. 67 2009 714 723
20. Recent works: H. Sashida, A. Nakayama, and M. Kaname Synthesis 2008 3229 3236
21. H. Sashida, S. Nakabayashi, M. Kaname, and M. Minoura Heterocycles 80 2010 1339 1352
22. H. Sashida, H. Satoh, K. Ohyanagi, and M. Kaname Molecules 15 2010 1466 1472
23. Sashida, H.; Kaname, M.; Ohyanagi, K. Heterocycles, in press, doi:10.3987/COM-10-S(E)15.
24. H. Sashida, M. Kaname, A. Nakayama, H. Suzuki, and M. Minoura Tetrahedron 66 2010 5149 5157
25. 3SSe: C, 50.32; H, 4.43. Found: C, 50.26; H, 4.46.
26. w = 0.0698, GOF = 1.040. CCDC-(Z)-6Ca for (Z)-6Ca contains the supplementary crystallographic data for this Letter. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/products/csd/request/.
27. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution, Universität Göttingen, 1997.
28. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, Universität Göttingen, 1997.