Furan ring opening-indole ring closure: SnCl 2-induced reductive transformation of difuryl(2-nitroaryl)methanes into 2-(2-acylvinyl)indoles

Tetrahedron

Volumn 68, Issue 22, 2012, Pages 4252-4258

  Uchuskin, Maxim G ^a   Molodtsova, Natalia V ^a   Abaev, Vladimir T ^b   Trushkov, Igor V ^c,d   Butin, Alexander V ^a,e  

^a KUBAN STATE TECHNOLOGICAL UNIVERSITY   (Russian Federation)

^b NORTH OSSETIAN STATE UNIVERSITY   (Russian Federation)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

^d Federal Research Center of Pediatric Hematology   (Russian Federation)

^e PERM STATE UNIVERSITY   (Russian Federation)

Author keywords

Furans; Indoles; Nitroarenes; Nitrosoarenes; Reduction; Ring closure; Ring opening

Indexed keywords

2 (2 ACYLVINYL) 3 (5 ALKYL 2 FURYL)INDOLE; ALCOHOL; BIS(5 ALKYL 2 FURYL)(2 NITROARYL)METHANE; FURAN; HYDROGEN PEROXIDE; INDOLE; INDOLE DERIVATIVE; METHANE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROPHILICITY; NUCLEOPHILICITY; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 84860489625     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.069     Document Type: Article

References (82)

1. R.J. Sundberg Indoles 1996 Academic San Diego, CA
2. T.L. Gilchrist J. Chem. Soc., Perkin Trans. 1 1999 2849 2866
3. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045 1075
4. M. Makosza, and K. Wojciechowski Heterocycles 54 2001 445 474
5. G. Battistuzzi, S. Cacchi, and G. Fabrizi Eur. J. Org. Chem. 2002 2671 2681
6. S. Cacchi, and G. Fabrizi Chem. Rev. 105 2005 2873 2920
7. G.R. Humphrey, and J.T. Kuethe Chem. Rev. 106 2006 2875 2911
8. A. Reissert Chem. Ber. 30 1897 1030 1053
9. F. Benington, R.D. Morin, and L.C. Clark J. Org. Chem. 25 1960 1542 1547
10. J. Bourdais, and C. Germain Tetrahedron Lett. 11 1970 195 198
11. R.D. Clark, and D.B. Repke Heterocycles 22 1984 195 221
12. M. Makosza, and J. Stalewski Tetrahedron 51 1995 7263 7276
13. M. Somei Chem. Pharm. Bull. 34 1986 4109 4115
14. S. Katayama, N. Ae, and R. Nagata J. Org. Chem. 66 2001 3474 3483
15. A. Wong, J.T. Kuethe, and I.W. Davies J. Org. Chem. 68 2003 9865 9866
16. A.G. Myers, and S.B. Herzon J. Am. Chem. Soc. 125 2003 12080 12081
17. K.C. Nicolaou, S.H. Lee, A.A. Estrada, and M. Zak Angew. Chem., Int. Ed. 44 2005 3736 3740
18. K.C. Nicolaou, A.A. Estrada, G.C. Freestone, S.H. Lee, and X. Alvarez-Mico Tetrahedron 63 2007 6088 6114
19. G. Bartoli, G. Palmieri, M. Bosco, and R. Dalpozzo Tetrahedron Lett. 30 1989 2129 2132
20. R. Dalpozzo, and G. Bartoli Curr. Org. Chem. 9 2005 163 178
21. K.R. Buszek, N. Brown, and D. Luo Org. Lett. 11 2009 201 204
22. Z. Wrobel, and M. Makosza Tetrahedron 53 1997 5501 5514
23. A. Stefanachi, F. Leonetti, A. Cappa, and A. Carotti Tetrahedron Lett. 44 2003 2121 2123
24. I.W. Davies, J.H. Smitrovich, R. Sidler, C. Qu, V. Gresham, and C. Bazaral Tetrahedron 61 2005 6425 6437
25. D. Alonso, E. Caballero, M. Medarde, and F. Tome Tetrahedron Lett. 46 2005 4839 4841
26. R.W. Clawson, R.E. Deavers, N.G. Akhmedov, and B.C.G. Söderberg Tetrahedron 62 2006 10829 10834
27. S.R. Banini, M.R. Turner, M.M. Cummings, and B.C.G. Söderberg Tetrahedron 67 2011 3603 3611
28. J.I.G. Cadogan Synthesis 1969 11 17
29. R.J. Sundberg J. Org. Chem. 30 1965 3604 3610
30. B.C. Söderberg, and J.A. Shriver J. Org. Chem. 62 1997 5838 5845
31. G. Jones, and W.H. McKinley J. Chem. Soc., Perkin Trans. 1 1979 599 602
32. G.R. Cliff, G. Jones, and J.Mc.K. Woollard J. Chem. Soc., Perkin Trans. 1 1974 2072 2076
33. S. Sharma, and B. Kundu Tetrahedron Lett. 49 2008 7062 7065
34. A.V. Butin, V.T. Abaev, T.A. Stroganova, and A.V. Gutnov Molecules 2 1997 62 68
35. V.T. Abaev, A.V. Gutnov, A.V. Butin, and V.E. Zavodnik Tetrahedron 56 2000 8933 8937
36. A.S.K. Hashmi, T.M. Frost, and J.W. Bats J. Am. Chem. Soc. 122 2000 11553 11554
37. K. Yamamura, S. Kawabata, T. Kimura, K. Eda, and M. Hashimoto J. Org. Chem. 70 2005 8902 8906
38. K. Tokumaru, S. Arai, and A. Nishida Org. Lett. 8 2006 27 30
39. I. Ueda, M. Nishiura, T. Takahashi, K. Eda, M. Hashimoto, and K. Yamamura Tetrahedron Lett. 47 2006 8535 8537
40. V.T. Abaev, F.A. Tsiunchik, A.V. Gutnov, and A.V. Butin J. Heterocycl. Chem. 45 2008 475 481
41. Y. Chen, Y. Lu, G. Li, and Y. Liu Org. Lett. 11 2009 3838 3841
42. H. Brice, and J. Clayden Chem. Commun. 2009 1964 1966
43. L.E. Kaim, L. Grimaud, and S. Wagschal Chem. Commun. 2011 1887 1889
44. H. Umemiya, H. Fukasawa, M. Ebisawa, L. Eyrolles, E. Kawachi, G. Eisenmann, H. Gronemeyer, Y. Hashimoto, K. Shudo, and H. Kagechika J. Med. Chem. 40 1997 4222 4234
45. J.I. Andres, J. Alcazar, J.M. Alonso, A. Diaz, J. Fernandez, P. Gil, L. Iturrino, E. Matesanz, T.F. Meert, A. Megens, and V.K. Sipido Bioorg. Med. Chem. Lett. 12 2002 243 248
46. J. Pawlowska, Z. Czarnocki, K. Wojtasiewicz, and J.K. Maurin Tetrahedron: Asymmetry 14 2003 3335 3342
47. F. Hunziker, R. Fischer, P. Kipfer, J. Schmutz, H.R. Bürki, E. Eichenberger, and T.G. White Eur. J. Med. Chem. 16 1981 391 398
48. A.V. Butin, F.A. Tsiunchik, O.N. Kostyukova, M.G. Uchuskin, and I.V. Trushkov Synthesis 2011 2629 2638
49. B. Kundu, D. Sawant, and R. Chhabra J. Comb. Chem. 7 2005 317 321
50. S. Duggineni, D. Sawant, B. Saha, and B. Kundu Tetrahedron 62 2006 3228 3241
51. E. David, S. Pellet-Rostaing, and M. Lemaire Tetrahedron 63 2007 8999 9006
52. P.K. Agarwal, M. Saifuddin, and B. Kundu Tetrahedron 66 2010 862 870
53. P.K. Agarwal, S.K. Sharma, D. Sawant, and B. Kundu Tetrahedron 65 2009 1153 1161
54. A.V. Butin, M.G. Uchuskin, A.S. Pilipenko, F.A. Tsiunchik, D.A. Cheshkov, and I.V. Trushkov Eur. J. Org. Chem. 2010 920 926
55. A.V. Butin, and S.K. Smirnov Tetrahedron Lett. 46 2005 8443 8445
56. A.V. Butin Tetrahedron Lett. 47 2006 4113 4116
57. A.V. Butin, S.K. Smirnov, and T.A. Stroganova J. Heterocycl. Chem. 43 2006 623 628
58. A.V. Butin, S.K. Smirnov, T.A. Stroganova, W. Bender, and G.D. Krapivin Tetrahedron 63 2007 474 491
59. A.V. Butin, S.K. Smirnov, and I.V. Trushkov Tetrahedron Lett. 49 2008 20 24
60. A.V. Butin, S.K. Smirnov, F.A. Tsiunchik, M.G. Uchuskin, and I.V. Trushkov Synthesis 2008 2943 2952
61. A.V. Butin, F.A. Tsiunchik, V.T. Abaev, and V.E. Zavodnik Synlett 2008 1145 1148
62. A.V. Butin, O.N. Kostyukova, F.A. Tsiunchik, M.G. Uchuskin, O.V. Serdyuk, and I.V. Trushkov J. Heterocycl. Chem. 48 2011 684 690
63. A.S. Pilipenko, V.V. Mel'chin, I.V. Trushkov, D.A. Cheshkov, and A.V. Butin Tetrahedron 68 2012 619 627
64. A. Penoni, and K.M. Nicholas Chem. Commun. 2002 484 485
65. A. Penoni, J. Volkmann, and K.M. Nicholas Org. Lett. 4 2002 699 701
66. F. Ragaini, A. Rapetti, E. Visentin, M. Monzani, A. Caselli, and S. Cenini J. Org. Chem. 71 2006 3748 3753
67. T.H.H. Hsieh, and V.M. Dong Tetrahedron 65 2009 3062 3068
68. A. Penoni, G. Palmisano, Y.-L. Zhao, K.N. Houk, J. Volkmann, and K.M. Nicholas J. Am. Chem. Soc. 131 2009 653 661
69. F. Tibiletti, M. Simonetti, K.M. Nicholas, G. Palmisano, M. Parravicini, F. Imbesi, S. Tollari, and A. Penoni Tetrahedron 66 2010 1280 1288
70. S. Murru, A.A. Gallo, and R.S. Srivastava ACS Catal. 1 2011 29 31
71. N. Matsumoto, and M. Takahashi Tetrahedron 58 2002 10073 10079
72. F.-L. Zhang, and A. Vasella Helv. Chim. Acta 91 2008 2351 2360
73. J.M. Wallace, B.C.G. Söderberg, J. Tamariz, N.G. Akhmedov, and M.T. Hurley Tetrahedron 64 2008 9675 9684
74. G.W. Amarante, M. Benassi, R.N. Pascoal, M.N. Eberlin, and F. Coelho Tetrahedron 66 2010 4370 4376
75. F. Sun, X. Zhao, and D. Shi Tetrahedron Lett. 52 2011 5633 5635
76. A. Kwast, K. Stachowska, A. Trawczynsky, and A. Wrobel Tetrahedron Lett. 52 2011 6484 6488
77. V.V. Pagar, A.M. Jadhav, and R.-S. Liu J. Am. Chem. Soc. 133 2011 20728 20731
78. M.G. Vetelino, and J.W. Coe Tetrahedron Lett. 35 1994 219 222
79. S. Kumar, E.J. Wachtel, and E. Keinan J. Org. Chem. 58 1993 3821 3827
80. X.-D. Xiong, W.-X. Chen, Y.-Y. Kuang, and F.-E. Chen Org. Prep. Proced. Int. 41 2009 423 427
81. J.E. Fitzpatrick, D.J. Milner, and P. White Synth. Commun. 12 1982 489 494
82. M.R. Michaelides, Y. Hong, S. DiDomenico, E.K. Bayburt, K.E. Asin, D.R. Britton, C.W. Lin, and K. Shiosaki J. Med. Chem. 40 1997 1585 1599