Furan ring opening - Indole ring closure: Pseudooxidative furan ring opening in the synthesis of indoles

Tetrahedron Letters

Volumn 46, Issue 48, 2005, Pages 8443-8445

  Butin, Alexander V ^a   Smirnov, Sergey K ^a  

^a KUBAN STATE TECHNOLOGICAL UNIVERSITY   (Russian Federation)

Author keywords

Furan; Indole; Recyclization

Indexed keywords

AMINE; BENZYL ALCOHOL DERIVATIVE; FURAN DERIVATIVE; INDOLE DERIVATIVE; METHANE;

ARTICLE; DRUG SYNTHESIS; ELIMINATION REACTION; OXIDATION; POLYMERIZATION; RING OPENING;

EID: 27644542181     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.057     Document Type: Article

References (37)

1. See the following reviews: C.J. Moody Synlett 1994 681 688
2. R.J. Sundberg Indoles 1996 Academic Press London
3. T.L. Gilchrist J. Chem. Soc., Perkin Trans. 1 1999 2849 2866
4. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045 1075
5. See for example: D.G. Powers, D.S. Casebier, D. Fokas, W.J. Ryan, J.R. Troth, and D.L. Coffen Tetrahedron 54 1998 4085 4096
6. G. McCort, O. Duclos, C. Cadilhac, and E. Guilpain Tetrahedron Lett. 40 1999 6211 6215
7. U. Pindur, and R. Adam Helv. Chim. Acta 73 1990 827 838
8. U. Pindur, and R. Adam Heterocycles 31 1990 587 592
9. M. Eitel, and U. Pindur J. Org. Chem. 55 1990 5368 5374
10. R.C. Larock, E.K. Yum, and M.D. Refvik J. Org. Chem. 63 1998 7652 7662
11. A.V. Sanin, V.G. Nenajdenko, K.I. Smolko, D.I. Denisenko, and E.S. Balenkova Synthesis 1998 842 846
12. F.E. Ziegler, E.B. Spitzner, and C.K. Wilkins J. Org. Chem. 36 1971 1759 1764
13. M. Pailer, E. Schaffer, and I. Schlaeger Monatsh. Chem. 110 1979 589 592
14. A.K. Mohanakrishnan, and P.C. Srinivasan J. Org. Chem. 60 1995 1939 1946
15. E.V. Sadanandan, M. Vedachalam, and P.C. Srinivasan Ind. J. Chem. 32B 1993 481 483
16. M. Eitel, and U. Pindur Synthesis 1989 364 367
17. V.A. Dombrovskii, E.V. Gracheva, and P.M. Kochergin Khim. Geterotsikl. Soedin. 1986 40 43
18. P.C. Hayes, G. Jones, C. Keates, I. Kladko, and P. Radley J. Chem. Res. (S) 1980 288
19. G. Jones, C. Keates, I. Kladko, and P. Radley Tetrahedron Lett. 20 1979 1445 1448
20. A.V. Butin, T.A. Stroganova, V.T. Abaev, and V.E. Zavodnik Khim. Geterotsikl. Soedin. 1997 1614 1621
21. A.V. Butin, V.T. Abaev, T.A. Stroganova, and A.V. Gutnov Molecules 2 1997 62 68
22. A.V. Butin, T.A. Stroganova, I.V. Lodina, and G.D. Krapivin Tetrahedron Lett. 42 2001 2031 2033
23. V.T. Abaev, A.V. Gutnov, and A.V. Butin Khim. Geterotsikl. Soedin. 1998 603 607
24. A.V. Gutnov, V.T. Abaev, A.V. Butin, and A.S. Dmitriev J. Org. Chem. 66 2001 8685 8686
25. V.T. Abaev, A.A. Osipova, and A.V. Butin Khim. Geterotsikl. Soedin. 2001 849 850
26. Ind), 8.09 (1H, d, J = 16.5 Hz, CH).
27. Tosylamide was isolated from the reaction mixture.
28. M.R. Iesce, F. Cermola, M.L. Grasiano, and R. Scarpati Synthesis 1994 944 948
29. K. Ito, and K. Yakushijin Heterocycles 9 1978 1603 1606
30. J. Jurczak, and S. Pikul Tetrahedron Lett. 26 1985 3039 3040
31. G. Piancatelli, A. Scettri, and M. D'Auria Tetrahedron 36 1980 661 663
32. A. D'Annibale, and A. Scettri Tetrahedron Lett. 36 1995 4659 4660
33. C. Dominguez, A.G. Csaky, and J. Plumet Tetrahedron Lett. 31 1990 7669 7670
34. See also the following review: G. Piancatelli, M. D'Auria, and F. D'Onofrio Synthesis 1994 867 889
35. V.T. Abaev, A.V. Gutnov, A.V. Butin, and V.E. Zavodnik Tetrahedron 56 2000 8933 8937
36. M. Sasabe, Y. Hounda, H. Takagi, T. Sugane, X. Bo, and K. Yamamura J. Chem. Soc., Perkin Trans. 1 2000 3786 3790
37. Bf), 7.49 (1H, d, J = 15.6 Hz, CH).