Intramolecular reactions of 2-indolylacyl Radicals: Access to 1,2-fused ring indole derivatives

Organic Letters

Volumn 6, Issue 5, 2004, Pages 759-762

  Bennasar, M Lluïsa ^a   Roca, Tomàs ^a   Ferrando, Francesc ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; INDOLE DERIVATIVE; RADICAL;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 1642334648     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036455l     Document Type: Article

References (36)

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10. For recent examples of the generation of acyl radicals from thiolesters, see: (a) Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566-3570. (b) Ozaki, S.; Adachi, M.; Sekiya, S.; Kamikawa, R. J. Org. Chem. 2003, 68, 4586-4589. (c) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S. Org. Lett. 2003, 5, 1313-1316. From acyl hydrazides, see: (d) Braslau, R.; Anderson, M. O.; Rivera, F.; Jiménez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513-5523. (e) Bath, S.; Laso, N. M.; López-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204-205.
11. For recent examples of the generation of acyl radicals from thiolesters, see: (a) Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566-3570. (b) Ozaki, S.; Adachi, M.; Sekiya, S.; Kamikawa, R. J. Org. Chem. 2003, 68, 4586-4589. (c) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S. Org. Lett. 2003, 5, 1313-1316. From acyl hydrazides, see: (d) Braslau, R.; Anderson, M. O.; Rivera, F.; Jiménez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513-5523. (e) Bath, S.; Laso, N. M.; López-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204-205.
12. For recent examples of the generation of acyl radicals from thiolesters, see: (a) Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566-3570. (b) Ozaki, S.; Adachi, M.; Sekiya, S.; Kamikawa, R. J. Org. Chem. 2003, 68, 4586-4589. (c) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S. Org. Lett. 2003, 5, 1313-1316. From acyl hydrazides, see: (d) Braslau, R.; Anderson, M. O.; Rivera, F.; Jiménez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513-5523. (e) Bath, S.; Laso, N. M.; López-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204-205.
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16. Bennasar, M.-L.; Roca, T.; Griera, R.; Bassa, M.; Bosch, J. J. Org. Chem. 2002, 67, 6268-6271.
17. For recent examples of intramolecular reactions of acyl radicals generated from alkyl phenyl selenoesters, see: (a) Double, P.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1998, 2005-2007. (b) Evans, P. A.; Raina, S.; Ahsan, K. Chem. Commun. 2001, 2504-2505 and references therein, (c) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890.
18. For recent examples of intramolecular reactions of acyl radicals generated from alkyl phenyl selenoesters, see: (a) Double, P.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1998, 2005-2007. (b) Evans, P. A.; Raina, S.; Ahsan, K. Chem. Commun. 2001, 2504-2505 and references therein, (c) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890.
19. For recent examples of intramolecular reactions of acyl radicals generated from alkyl phenyl selenoesters, see: (a) Double, P.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1998, 2005-2007. (b) Evans, P. A.; Raina, S.; Ahsan, K. Chem. Commun. 2001, 2504-2505 and references therein, (c) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890.
20. For related cyclizations involving 2-indolyl radicals, see: Dobbs, A. P. ; Jones, K.; Veal, K. T. Tetrahedron 1998, 54, 2149-2160.
21. See the Supporting Information for complete details.
22. Batty, D.; Crich, D. Synthesis 1990, 273-275.
23. Tetracycle 7 has been prepared by cyclization of a 2-indolylacyl radical generated from an alkynylthiol ester. See ref 4c.
24. Remers, W. A.; Dorr, R. T. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1988; Vol. 6, pp 1-74.
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26. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
27. For similar 5-exo cyclizations - intermolecular additions, see: (a) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc. 1990, 112, 4003-4008. (b) Tsunoi, S.; Ryu, I.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Synlett 1995, 1249-1251.
28. For similar 5-exo cyclizations - intermolecular additions, see: (a) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc. 1990, 112, 4003-4008. (b) Tsunoi, S.; Ryu, I.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Synlett 1995, 1249-1251.
29. Curran, D. P.; Porter, N. A. Giese, B. Stereochemistry of Radical Reactions; WCH: Weinheim, 1996.
30. For a discussion, see: Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Venturini, A.; Zavitsas, A. A. Chem. Eur. J. 1997, 3, 376-387. See also ref 6.
31. Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Aust. J. Chem. 1972, 25, 1081-1105.
32. In the literature, there are several reports of alkyl and aryl radical cyclizations upon azacyclic systems, most of them 1,4,5,6-tetrahydropyridines, to give heterocycles bearing the nitrogen atom in the new ring formed. See inter alia: (a) Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. (b) Zhang, W. Tetrahedron 2001, 57, 7237-7262. (c) Zhang, W.; Pugh, G. Tetrahedron 2003, 59, 3009-3018. For radical cyclizations upon 1,4,5,6-tetrahidropyridines where a carbocycle is created, see: (d) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84-91. (e) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.
33. In the literature, there are several reports of alkyl and aryl radical cyclizations upon azacyclic systems, most of them 1,4,5,6-tetrahydropyridines, to give heterocycles bearing the nitrogen atom in the new ring formed. See inter alia: (a) Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. (b) Zhang, W. Tetrahedron 2001, 57, 7237-7262. (c) Zhang, W.; Pugh, G. Tetrahedron 2003, 59, 3009-3018. For radical cyclizations upon 1,4,5,6-tetrahidropyridines where a carbocycle is created, see: (d) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84-91. (e) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.
34. In the literature, there are several reports of alkyl and aryl radical cyclizations upon azacyclic systems, most of them 1,4,5,6-tetrahydropyridines, to give heterocycles bearing the nitrogen atom in the new ring formed. See inter alia: (a) Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. (b) Zhang, W. Tetrahedron 2001, 57, 7237-7262. (c) Zhang, W.; Pugh, G. Tetrahedron 2003, 59, 3009-3018. For radical cyclizations upon 1,4,5,6-tetrahidropyridines where a carbocycle is created, see: (d) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84-91. (e) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.
35. In the literature, there are several reports of alkyl and aryl radical cyclizations upon azacyclic systems, most of them 1,4,5,6-tetrahydropyridines, to give heterocycles bearing the nitrogen atom in the new ring formed. See inter alia: (a) Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. (b) Zhang, W. Tetrahedron 2001, 57, 7237-7262. (c) Zhang, W.; Pugh, G. Tetrahedron 2003, 59, 3009-3018. For radical cyclizations upon 1,4,5,6-tetrahidropyridines where a carbocycle is created, see: (d) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84-91. (e) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.
36. In the literature, there are several reports of alkyl and aryl radical cyclizations upon azacyclic systems, most of them 1,4,5,6-tetrahydropyridines, to give heterocycles bearing the nitrogen atom in the new ring formed. See inter alia: (a) Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. (b) Zhang, W. Tetrahedron 2001, 57, 7237-7262. (c) Zhang, W.; Pugh, G. Tetrahedron 2003, 59, 3009-3018. For radical cyclizations upon 1,4,5,6-tetrahidropyridines where a carbocycle is created, see: (d) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84-91. (e) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.