Regioselective synthesis of indole-annulated sulfur heterocycles by tri-n-butyltin hydride-mediated aryl radical cyclization

Journal of Sulfur Chemistry

Volumn 29, Issue 5, 2008, Pages 467-474

  Majumdar, K C ^a   Debnath, P ^a   Alam, S ^a   Islam, R ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

6 endo trig; Aryl radical cyclization; Bu3SnH AIBN; Indole; Sulfur heterocycles

Indexed keywords

CYCLIZATION; REGIOSELECTIVITY; SULFUR;

6-ENDO-TRIG; ARYL RADICAL CYCLIZATION; BU3SNH-AIBN; CYCLIZATIONS; INDOLE; REGIOSELECTIVE SYNTHESIS; SULFUR HETEROCYCLES; TRI-N-BUTYLTIN;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 54049089226     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990802105788     Document Type: Article

References (41)

1. (a) Giese, B. Radicals in Organic Synthesis: Formation f Carbon-Carbon Bonds; Pergamon: New York, 1986;
2. (b) Ishibashi, H.; Ohata, K.; Niihara, M.; Sato, T.; Ikeda, M. J. Chem. Soc., Perkin Trans. I 2000, 547-553;
3. (c) Parsons, A.F.; Williams, D.A.J. Tetrahedron 2000, 56, 7217-7228;
4. (d) Curran, D.P. Synthesis 1988, 417-439;
5. (e) Curran, D.P. Synthesis 1988, 489-513;
6. (f) Renaud, P.; Sibi, M. Eds.; Radicals in Organic Synthesis, Vols. 1 and 2; Wiley-VCH: Weinheim, 2001;
7. (g) Majumdar, K.C.; Basu, P.K. Heterocycles 2002, 57, 2413-2440;
8. (h) Majumdar, K.C.; Basu, P.K.; Mukhopadhyay, P.P. Tetrahedron 2005, 61, 10603-10642;
9. (i) Majumdar, K.C.; Basu, P.K.; Chattopadhyay, S.K. Tetrahedron 2007, 63, 793-826.
10. Bowman, W.R.; Storey, J.D. Chem. Soc. Rev. 2007, 36, 1803-1822.
11. (a) Majumdar, K.C.; Biswas, A.; Mukhopadhyay, P.P. Synthesis 2003, 2385-2389;
12. (b) Majumdar, K.C.; Mukhopadhyay, P.P. Biswas. Tetrahedron Lett. 2005, 46, 6655-6658;
13. (c) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo. P.; Strazzari, S. Org. Lett. 2003, 5, 1313-1316;
14. (d) Benati, L.; Bencivenni, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo. P.; Zanardi, G. J. Org. Chem. 2006, 71, 3192-3197;
15. (e) Benati, L. Capella, L.; Montevecchi, P.C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941-7946;
16. (f) Della, E.W.; Graney, S.D. Org. Lett. 2002, 4, 4065-4067;
17. (g) Bencivenni, G.; Lanza, T.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Zanardi, G. Org. Lett. 2008, 9, 1061.
18. Flanagan, S.R.; Harrowven, D.C. Tetrahedron Lett. 2003, 44, 1795-1798.
19. Cai, Y.; Dang, H.S.; Roberts, B.P. J. Chem. Soc., Perkin Trans. I 2002, 2449-2458.
20. (a) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175-191;
21. (b) Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148-180;
22. (c) Wacker, D.A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191;
23. (d) Smart, B.P.; Oslund, R.C.; Walsh, L.A.; Gelb, M.H. J. Med. Chem. 2006, 49, 2858-2860;
24. (e) Sundberg, R.J.; Indoles; Academic Press: London, 1996;
25. (f) Yamanaka, E.; One, M.; Kasamatsu, S.; Aimi, N.; Sakai, S. Chem. Pharm. Bull. 1984, 32, 818-821;
26. (g) Sakai, S.; Aimi, N.; Yamaguchi, K.; Hitotsuyonagi, Y.; Watanabe, C.; Yokose, K.; Koyama, Y.; Shudo, K.; Itai, A. Chem. Pharm. Bull. 1984, 32, 354-357.
27. (a) Takasugi, M.; Katsui, N.; Shirata, A. J. Chem. Soc., Chem. Commun. 1986, 1077-1078;
28. (b) Takasugi, M.; Monde, K.; Katsui, N.; Shirata, A. Bull. Chem. Soc. Jpn. 1988, 61, 285-289;
29. (c) Takasugi, M.; Monde, K.; Katsui, N.; Shirata, A. Chem. Lett. 1987, 1631-1632.
30. For a recent reviews of indole phytoalexins, see: Pedras, M.S.C.; Okanga, F.I.; Zaharia, I.L.; Khan, A.Q. Phytochemistry 2000, 53, 161-176.
31. (a) Mehta, R.G.; Liu, J.; Constantinou, A.; Hawthorne, M.; Pezzuto, J.M.; Moon, R.C.; Moriarty, R.M. Anticancer Res. 1994, 14, 1209-1214;
32. (b) Mehta, R.G., Liu, J., Constantinou, A., Thomas, C.F., Hawthorne, M., You, M., Gerhäuser, C., Pezzuto, J.M., Moon, R.C.; Moriarty, R.M. Carcinogenesis 1995, 16, 399-404.
33. Baur, R.; Stadler, E.; Monde, K.; Takasugi, M. Chemoecology 1998, 8, 163-168.
34. (a) Takada, S.; Makisumi, Y. Chem. Pharm. Bull. 1984, 32, 872-876;
35. (b) Takada, S.; Ishizuka, N.; Sasatani, T.; Makisumi, Y.; Jyoyama, H.; Hatakeyama, H.; Asanuma, F.; Hirose, K. Chem. Pharm. Bull. 1984, 32, 877-886.
36. Makisumi, Y.; Satatani, T. US Patent: 4,910,318, March 20, 1990.
37. (a) Clyne, M.A.; Aldabbagh, F. Org & Biomol. Chem. 2006, 4, 268-277;
38. (b) McLoughlin, P.T.F.; Clyne, M.A.; Aldabbagh, F. Tetrahedron 2004, 60, 8065-8071.
39. Abeywickrema, A.N.; Beckwith, A.L.J.; Gerba, S. J. Org. Chem. 1987, 52, 4072-4078.
40. Chatgilialoglu, C.; Altieri, A.; Fischer, H . J. Am. Chem. Soc. 2002, 124, 12816-12823.
41. Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667.