Reactions of selenium dichloride and dibromide with unsaturated ethers. Annulation of 2,3-dihydro-1,4-oxaselenine to the benzene ring

Tetrahedron Letters

Volumn 52, Issue 36, 2011, Pages 4606-4610

  Potapov, Vladimir A ^a   Musalov, Maxim V ^a   Amosova, Svetlana V ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

2,3 Dihydro 1,4 oxaselenine; Allyl phenyl ether; Propargyl phenyl ether; Selenium dibromide; Selenium dichloride; Unsaturated ethers; Vinylic selenides

Indexed keywords

3 CHLOROMETHYL 2,3 DIHYDRO 1,4 BENZOXASELENINE; 3 CHLOROMETHYL 2,3 DIHYDRO 1,4 OXASELENINE; 3 CHLOROMETHYLENE 2,3 DIHYDRO 1,4 BENZOXASELENINE; 3 CHLOROMETHYLENE 2,3 DIHYDRO 1,4 OXASELENINE; BENZENE; BIS(2 BUTOXY 2 BROMOETHYL)SELENIDE; BIS(2 BUTOXY 2 CHLOROETHYL)SELENIDE; BIS(2 ISOBUTOXY 2 BROMOETHYL)SELENIDE; BIS(2 ISOBUTOXY 2 CHLOROETHYL)SELENIDE; BIS(3 PHENOXY 1 BROMO 1 PROPEN 2 YL)SELENIDE; BIS(3 PHENOXY 1 CHLORO 1 PROPEN 2 YL)SELENIDE; BIS(3 PHENYLOXY 2 BROMOPROPYL)SELENIDE; BIS(3 PHENYLOXY 2 CHLOROPROPYL)SELENIDE; ETHER; SELENIUM; SELENIUM DIBROMIDE; SELENIUM DICHLORIDE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; SYNTHESIS;

EID: 79961170320     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.071     Document Type: Article

References (59)

1. K. Schwarz, and C.M. Foltz J. Am. Chem. Soc. 79 1957 3292
2. K.C. Nicolaou, and N.A. Petasi Selenium in Natural Products Synthesis 1984 CIS Philadelphia
3. C. Paulmier Selenium Reagents and Intermediates in Organic Synthesis 1986 Pergamon Oxford
4. S. Patai, and Z. Rappoport The Chemistry of Organic Selenium and Tellurium Compounds 1986 Wiley New York
5. D. Liotta Organoselenium Chemistry 1987 Wiley New York
6. A. Krief, and L. Hevesi Organoselenium Chemistry I 1988 Springer Berlin
7. T.G. Back Organoselenium Chemistry: A Pratical Approach 1999 Oxford University Press Oxford
8. V.A. Potapov, and B.A. Trofimov Sci. Synth. 24 2005 957
9. T. Wirth Organoselenium Chemistry - Modern Developments in Organic Synthesis, Topics in Current Chemistry 208 2000 Spring-Verlag Heidelberg, Germany
10. G. Mugesh, W.-W. du Mont, and H. Sies Chem. Rev. 101 2001 2125
11. C.W. Nogueira, G. Zeni, and J.B.T. Rocha Chem. Rev. 104 2004 6255
12. K.C. Nicolaou Tetrahedron 37 1981 4087
13. N. Petragnani, H.A. Stefani, and C.J. Valduga Tetrahedron 57 2001 1411
14. T.G. Back D. Liotta, Organoselenium Chemistry 1987 John Wiley New York 1
15. G.H. Shmid S. Patai, The Chemistry of the Carbon-Carbon Triple Bond 1978 John Wiley Chichester 275
16. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov Tetrahedron Lett. 50 2009 306
17. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov J. Organomet. Chem. 694 2009 3369
18. V.A. Potapov, V.A. Shagun, M.V. Penzik, and S.V. Amosova J. Organomet. Chem. 695 2010 1603
19. S.V. Amosova, M.V. Penzik, V.A. Potapov, and A.I. Albanov Russ. Chem. Bull. Int. Ed. 2008 1323
20. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov Russ. J. Gen. Chem. 79 2009 161
21. V.A. Potapov, S.V. Amosova, K.A. Volkova, M.V. Penzik, and A.I. Albanov Tetrahedron Lett. 51 2010 89
22. V.A. Potapov, K.A. Volkova, M.V. Penzik, A.I. Albanov, and S.V. Amosova Russ. J. Gen. Chem. 79 2009 1225
23. V.A. Potapov, K.A. Volkova, M.V. Penzik, A.I. Albanov, and S.V. Amosova Russ. J. Org. Chem. 44 2008 1556
24. V.A. Potapov, K.A. Volkova, M.V. Penzik, A.I. Albanov, and S.V. Amosova Russ. J. Gen. Chem. 78 2008 1990
25. V.A. Potapov, E.O. Kurkutov, M.V. Musalov, and S.V. Amosova Tetrahedron Lett. 51 2010 5258
26. V.A. Potapov, E.O. Kurkutov, A.I. Albanov, and S.V. Amosova Russ. J. Org. Chem. 44 2008 1547
27. V.A. Potapov, E.O. Kurkutov, and S.V. Amosova Russ. J. Org. Chem. 46 2010 1099
28. V.A. Potapov, E.O. Kurkutov, and S.V. Amosova Russ. J. Gen. Chem. 80 2010 1220
29. V.A. Potapov, S.V. Amosova, O.V. Belozerova, A.I. Albanov, O.G. Yarosh, and M.G. Voronkov Chem. Heterocycl. Compd. 39 2003 549
30. V.A. Potapov, and S.V. Amosova Russ. J. Org. Chem. 39 2003 1373
31. S.V. Amosova, and A.V. Martynov Mini-Rev. Org. Chem. 7 2010 23
32. V.A. Potapov, O.I. Khuriganova, M.V. Musalov, L.I. Larina, and S.V. Amosova Russ. J. Gen. Chem. 80 2010 541
33. V.A. Potapov, M.V. Musalov, O.I. Khuriganova, L.I. Larina, and S.V. Amosova Russ. J. Org. Chem. 46 2010 753
34. V.A. Potapov, O.I. Khuriganova, and S.V. Amosova Russ. J. Org. Chem. 46 2010 1421
35. V.A. Potapov, O.I. Khuriganova, and S.V. Amosova Russ. J. Org. Chem. 45 2009 1569
36. S.V. Amosova, E.V. Abramova, and V.A. Potapov Russ. J. Gen. Chem. 78 2008 1463
37. S.V. Amosova, M.V. Penzik, A.I. Albanov, and V.A. Potapov Russ. J. Org. Chem. 45 2009 1271
38. V.A. Potapov, K.A. Volkova, and S.V. Amosova Russ. J. Gen. Chem. 79 2009 1758
39. A.A. Accurso, S.-H. Cho, A. Amin, V.A. Potapov, S.V. Amosova, and M.G. Finn J. Org. Chem. 76 2011 4392
40. E. Nagy-Felsobuki, and J.B. Peel Chem. Phys. 45 1980 189
41. J. Milne Polyhedron 4 1985 65
42. M. Lamoureux, and J. Milne Polyhedron 9 1990 589
43. R. Steudel, D. Jensen, and F. Baumgart Polyhedron 9 1990 1199
44. G. Perin, E.J. Lenardão, R.G. Jacob, and R.B. Panatieri Chem. Rev. 109 2009 1277
45. J.V. Comasseto, L.W. Ling, N. Petragnani, and H.A. Stefani Synthesis 1997 373
46. V.A. Potapov, and S.V. Amosova Russ. J. Org. Chem. 32 1996 1142
47. A.V. Martynov, V.A. Potapov, S.V. Amosova, N.A. Makhaeva, I.P. Beletskaya, and L. Hevesi J. Organomet. Chem. 674 2003 101
48. V.A. Potapov, S.V. Amosova, G.N. Dudareva, V.Yu. Shestakova, A.R. Zhnikin, B.V. Petrov, and T.N. Aksamentova Rec. Trav. Chim. 115 1996 443
49. V.A. Potapov, S.V. Amosova, and B.V. Petrov Phosphorus, Sulfur Silicon Relat. Elem. 136-138 1998 587
50. A.V. Martynov, V.A. Potapov, S.V. Amosova, and A.I. Albanov Russ. J. Gen. Chem. 73 2003 1398
51. J.V. Comasseto J. Organomet. Chem. 253 1983 131
52. V.A. Potapov, and S.V. Amosova Phosphorus, Sulfur Silicon Relat. Elem. 79 1993 277
53. V.A. Potapov, S.V. Amosova, and V.Yu. Shestakova Phosphorus, Sulfur Silicon Relat. Elem. 136-138 1998 205
54. S.V. Amosova, V.N. Elokhina, A.S. Nakhmanovich, L.I. Larina, A.V. Martynov, B.R. Steele, and V.A. Potapov Tetrahedron Lett. 49 2008 974
55. V.A. Potapov, V.N. Elokhina, L.I. Larina, T.I. Yaroshenko, A.A. Tatarinova, and S.V. Amosova J. Organomet. Chem. 694 2009 3679
56. J.V. Comasseto, J.T.B. Ferreira, and N. Petragnani J. Organomet. Chem. 216 1981 287
57. S.B. Needleman, and M.C. Chang Kuo Chem. Rev. 62 1962 405
58. M.F. Shostakovskii, A.V. Bogdanova, and A.N. Volkov Russ. Chem. Bull. 10 1961 1930
59. N.D. Luthra, and J.D. Odom Z. Rappoport, S. Patai, The Chemistry of Organic Selenium and Tellurium Compounds Vol. 1 1986 John Wiley New York 189