Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

Tetrahedron

Volumn 63, Issue 2, 2007, Pages 474-491

  Butin, Alexander V ^a   Smirnov, Sergey K ^a   Stroganova, Tatyana A ^a   Bender, Wolfgang ^b   Krapivin, Gennady D ^a  

^a KUBAN STATE TECHNOLOGICAL UNIVERSITY   (Russian Federation)

^b BAYER PHARMA AG   (Germany)

Author keywords

Furan; Indoles; Recyclization

Indexed keywords

ACETONE; FURAN DERIVATIVE; INDOLE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 33751510646     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.056     Document Type: Article

References (82)

1. See the following reviews:
2. Moody C.J. Synlett (1994) 681-688
3. Sundberg R.J. Indoles (1996), Academic, London
4. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1 (1999) 2849-2866
5. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045-1075
6. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1 (2001) 2491-2515
7. Taga M., Ohtsuka H., Inoune I., Kawaguchi T., Nomura S., Yamada K., Date T., Hiramutsu H., and Sato Y. Heterocycles 42 (1996) 251-263
8. Shin C., Yamada Y., Hayashi K., Yonezawa Y., Umemura K., Tanji T., and Yoshimura J. Heterocycles 43 (1996) 891-898
9. Wang Z., and Jimenez L.S. J. Org. Chem. 61 (1996) 816-818
10. Dong W., and Jimenez L.S. J. Org. Chem. 64 (1999) 2520-2523
11. Katayama S., Ae N., and Nagata R. J. Org. Chem. 66 (2001) 3474-3483
12. Cushing T.D., Sanz-Cervera J.F., and Williams R.M. J. Am. Chem. Soc. 118 (1996) 557-579
13. Kozmin S.A., and Rawal V.H. J. Am. Chem. Soc. 120 (1998) 13523-13524
14. Alvarez M., Bros M.A., and Joule J.A. Tetrahedron Lett. 39 (1998) 679-680
15. Wong A., Kuethe J.T., Davies I.W., and Hughes D.L. J. Org. Chem. 69 (2004) 7761-7764
16. Iwama T., Birman V.B., Kozmin S.A., and Rawal V.H. Org. Lett. 1 (1999) 673-676
17. Suzuki H., Gyoutoku H., Yokoo H., Shibna M., Sato Y., Yamada H., and Murakami Y. Synlett (2000) 1196-1198
18. Rutherford J.L., Rainka M.P., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 15168-15169
19. Banwell M.G., Kelly B.D., Kokas O.J., and Lupton D.W. Org. Lett. 5 (2003) 2497-2500
20. Gallou F., Yee N., Qiu F., Senanayake C., Linz G., Schnaubelt J., and Soyka R. Synlett (2004) 883-885
21. Ochi M., Kataoka K., Ariki S., Iwatsuki C., Kodama M., and Fukuyama Y. J. Nat. Prod. 61 (1998) 1043-1045
22. Hume W.E., Tokunaga T., and Nagata R. Tetrahedron 58 (2002) 3605-3611
23. Faul M.M., Grutsch J.L., Kobierski M.E., Kopach M.E., Krumrich C.A., Staszak M.A., Udodong U., Vicenzi J.T., and Sullivan K.A. Tetrahedron 59 (2003) 7215-7229
24. Fetter J., Bertha F., Poszavacz L., and Simig G. J. Heterocycl. Chem. 42 (2005) 137-139
25. Tsuji Y., Kotachi S., Huh K.-T., and Watanabe Y. J. Org. Chem. 55 (1990) 580-584
26. Webb R.R., Venuti M.C., and Eigenbrot C. J. Org. Chem. 56 (1991) 4706-4713
27. Aoyagi Y., Mizusaki T., and Ohta A. Tetrahedron Lett. 37 (1996) 9203-9206
28. Fujita K.-I., Yamomoto K., and Yamaguchi R. Org. Lett. 4 (2002) 2691-2694
29. Danishefsky S.J., and Phillips G.B. Tetrahedron Lett. 25 (1984) 3159-3162
30. Maehr H., and Smallheer J. J. Am. Chem. Soc. 107 (1985) 2943-2945
31. Ziegler F.E., and Berlin M.Y. Tetrahedron Lett. 39 (1998) 2455-2458
32. Banfield S.C., England D.B., and Kerr M.A. Org. Lett. 3 (2001) 3325-3327
33. Zawada P.V., Banfield S.C., and Kerr M.A. Synlett (2003) 971-974
34. Makoza M., and Stalewski J. Tetrahedron 51 (1995) 7263-7276
35. Makoza M., Stalewski J., and Maslennikova O.S. Synthesis (1997) 1131-1133
36. Belley M., Scheigetz J., Dube P., and Dolman S. Synlett (2001) 222-225
37. Walkington A., Gray M., Hossner F., Kitteringham J., and Voyle M. Synth. Commun. 33 (2003) 2229-2233
38. Samizu K., and Ogasawara K. Synlett (1994) 499-500
39. Sakagami H., and Ogasawara K. Heterocycles 51 (1999) 1131-1135
40. Alper P.B., and Nguyen K.T. J. Org. Chem. 68 (2003) 2051-2053
41. Cnilin A., Rodighiero P., and Guiotto A. Synthesis (1998) 309-312
42. See the following reviews:
43. Dean F.M. Adv. Heterocycl. Chem. 30 (1982) 167-238
44. Dean F.M. Adv. Heterocycl. Chem. 31 (1982) 237-344
45. Piancatelli G., D'Auria M., and D'Onofrio F. Synthesis (1994) 867-889
46. Abaev V.T., Gutnov A.V., and Butin A.V. Khim. Geterotsikl. Soedin (1998) 603-607
47. Abaev V.T., Osipova A.A., and Butin A.V. Khim. Geterotsikl. Soedin. (2001) 849-850
48. Gutnov A.V., Abaev V.T., Butin A.V., and Dmitriev A.S. J. Org. Chem. 66 (2001) 8685-8686
49. Butin A.V., Abaev V.T., Mel'chin V.V., and Dmitriev A.S. Tetrahedron Lett. 46 (2005) 8439-8441
50. See the following review:
51. Butin A.V., and Abaev V.T. Izv. Akad. Nauk, Ser. Khim. (2001) 1436-1443
52. Butin A.V., Stroganova T.A., Lodina I.V., and Krapivin G.D. Tetrahedron Lett. 42 (2001) 2031-2033
53. Ziegler F.E., Spitzner E.B., and Wilkins C.K. J. Org. Chem. 36 (1971) 1759-1764
54. Vedachalam M., Mohan B., and Srinivasan P.C. Tetrahedron Lett. 24 (1983) 3531-3532
55. Sadanandan E.V., Vedachalam M., and Srinivasan P.C. Indian J. Chem., Sect. B 32B (1993) 481-483
56. Lee J., Ha J.D., and Cha J.K. J. Am. Chem. Soc. 119 (1997) 8127-8128
57. Garnick R.L., Levery S.B., and Le Quesne P.W. J. Org. Chem. 43 (1978) 1226-1229
58. Iqbal Z., Jackson A.H., and Rao K.R.N. Tetrahedron Lett. 29 (1988) 2577-2580
59. Dujardin G., and Poirier J.-M. Bull. Soc. Franc 131 (1994) 900-909
60. Srivastava N., and Banik B.K. J. Org. Chem. 68 (2003) 2109-2114
61. Bartoli G., Bartolacci M., Bosco M., Foglia G., Giuliani A., Marcantoni E., Sambri L., and Torregiani E. J. Org. Chem. 68 (2003) 4594-4597
62. Arcadi A., Bianchi G., Chiarini M., D'Annibale G., and Marinelli F. Synlett (2004) 944-950
63. Cavdar H., and Saracoglu N. Tetrahedron 61 (2005) 2401-2405
64. Kul'nevich V.G., and Zhuravlev S.V. Khim. Geterotsikl. Soedin (1984) 307-308
65. Gutnov A.V., Butin A.V., Abaev V.T., Krapivin G.D., and Zavodnik V.E. Molecules 4 (1999) 204-218
66. See the following review:
67. Butin A.V., Stroganova T.A., and Kul'nevich V.G. Khim. Geterotsikl. Soedin (1999) 867-901
68. As a typical procedure, see:
69. Kamath H.V., Dhekne V.V., and Kulkarni S.N. Indian J. Chem., Sect. B 21B (1982) 911-913
70. Org. Synth. 32 (1952) 8-13
71. Davis R.B., and Pizzini L.C. J. Org. Chem. 25 (1960) 1884-1888
72. Ono A., Suzuki N., and Kamimura J. Synthesis (1987) 736-738
73. 2=0.0800. Crystallographic data (excluding structure factors) for the structure in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 601089. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]. Each request should be accompanied by the complete citation of this paper.
74. Butin A.V., Smirnov S.K., and Stroganova T.A. J. Heterocycl. Chem. 43 (2006) 623-628
75. Itoh T., Yokoya M., Miyauchi K., Nagata K., and Ohsawa A. Org. Lett. 5 (2003) 4301-4304
76. Haskins C.M., and Knight D.W. Tetrahedron Lett. 45 (2004) 599-601
77. Strekowski L., Aken K.V., and Gulevich Y. J. Heterocycl. Chem. 37 (2000) 1495-1499
78. Fresneda P.M., Molina P., and Bleda J.A. Tetrahedron 57 (2001) 2355-2363
79. Tanaka K., and Katsumura S. J. Am. Chem. Soc. 124 (2002) 9660-9661
80. McClenaghan N.D., Passalacqua R., Loiseau F., Campagna S., Verheyde B., Hameurlaine A., and Dehaen W. J. Am. Chem. Soc. 125 (2003) 5356-5365
81. Cheng K.-F., Wong T.-T., Wong W.-T., and Lai T.-F. J. Chem. Soc., Perkin Trans. 1 (1990) 2487-2496
82. Phisalaphong C., Takayama H., and Sakai S.-I. Tetrahedron Lett. 34 (1993) 4035-4038