Formation of a ten-membered lactam by chloroacetamide photocyclization on the indole 4-position

Heterocycles

Volumn 43, Issue 9, 1996, Pages 1959-1966

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Ramírez, Antonio ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000193083     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7533     Document Type: Article

References (25)

1. M.-L. Bennasar, E. Zulaica, A. Ramírez, and J. Bosch, J. Org. Chem., 1996, 61, 1239.
2. (a) J. A. Joule, "Indoles, The Monoterpenoid Indole Alkaloids", ed. by J. E. Saxton, in "The Chemistry of Heterocyclic Compounds", Vol. 25, Part 4, ed. by A. Weissberger and E. C. Taylor, Wiley, New York, 1983, pp. 244-264.
3. (b) J. A. Joule and M. Alvarez, "Monoterpenoid Indole Alkaloids", ed. by J. E. Saxton, in "The Chemistry of Heterocyclic Compounds", Vol. 25, Supplement to Part 4, ed. by E. C. Taylor, Wiley, Chichester, 1994, pp. 248-259.
4. The biogenetic numbering is used throughout this paper. J. Le Men and W.I. Taylor, Experientia, 1965, 21, 508.
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7. R. J. Sundberg, "Organic Photochemistry", Vol. 6, ed. by A. Padwa, Marcel Dekker, New York, 1983, pp. 121-176.
8. S. Naruto and O. Yonemitsu, Chem. Pharm. Bull, 1980, 28, 900.
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10. T. G. Back, D. L. Baron, and K. Yang, J. Org. Chem., 1993, 58, 2407.
11. (a) R. Huisgen and H. Walz, Chem. Ber., 1956, 89, 2616.
12. (b) R. M. Moriarty, J. Org. Chem., 1964, 29, 2748.
13. (c) R. M. Moriarty and J. M. Kliegman, J. Org. Chem., 1966, 31, 3007.
14. (d) Y. Endo, K. Shudo, A. Itai, M. Hasegawa, and S. Sakai, Tetrahedron, 1986, 42, 5905.
15. 11. (a) For the first example of hindered ring inversion of a medium-size bridged lactam, see: K. Hemmi, H. Nakai, S. Naruto, and O. Yonemitsu, J. Chem. Soc., Parkin Trans. II, 1972, 2252. For the formation of isolable atropisomers as a consequence of a restricted conformational change in eight-and nine-membered bridged lactams, see: (b) R. J. Sundberg and F. X. Smith, J. Org. Chem., 1975, 40, 2613. (c) R. J. Sundberg, J. G. Luis, R. L. Parton, S. Schreiber, P. C. Srinivasan, P. Lamb, P. Forcier, and R. F. Bryan, J. Org. Chem., 1978, 43, 4859.
16. (a) For the first example of hindered ring inversion of a medium-size bridged lactam, see: K. Hemmi, H. Nakai, S. Naruto, and O. Yonemitsu, J. Chem. Soc., Parkin Trans. II, 1972, 2252. For the formation of isolable atropisomers as a consequence of a restricted conformational change in eight-and nine-membered bridged lactams, see: (b) R. J. Sundberg and F. X. Smith, J. Org. Chem., 1975, 40, 2613. (c) R. J. Sundberg, J. G. Luis, R. L. Parton, S. Schreiber, P. C. Srinivasan, P. Lamb, P. Forcier, and R. F. Bryan, J. Org. Chem., 1978, 43, 4859.
17. (a) For the first example of hindered ring inversion of a medium-size bridged lactam, see: K. Hemmi, H. Nakai, S. Naruto, and O. Yonemitsu, J. Chem. Soc., Parkin Trans. II, 1972, 2252. For the formation of isolable atropisomers as a consequence of a restricted conformational change in eight-and nine-membered bridged lactams, see: (b) R. J. Sundberg and F. X. Smith, J. Org. Chem., 1975, 40, 2613. (c) R. J. Sundberg, J. G. Luis, R. L. Parton, S. Schreiber, P. C. Srinivasan, P. Lamb, P. Forcier, and R. F. Bryan, J. Org. Chem., 1978, 43, 4859.
18. AM1 minimized structures. Hyperchem: Autodesk Inc. 1992.
19. (a) T. Gallagher, P. Magnus, and J. C. Huffman, J. Am. Chem. Soc., 1983, 105, 4750.
20. (b) J. Bosch, M. Amat, E. Sanfeliu, and M. A. Miranda, Tetrahedron, 1985, 41, 2557.
21. 14. However, see: O. Schindler, P. Niklaus, U. Stauss, and H. P. Härter, Helv. Chim. Acta, 1976, 59, 2704. In contrast, there are some examples of photo-Fries rearrangements involving an intramolecular photochemical [1,3]-acyl migration from 1-acyl-3-alkylindoles to the corresponding 3-acylindolenines: Y. Ban, K. Yoshida. J. Goto, T. Oishi, and E. Takeda, Tetrahedron, 1983, 39, 3657.
22. However, see: O. Schindler, P. Niklaus, U. Stauss, and H. P. Härter, Helv. Chim. Acta, 1976, 59, 2704. In contrast, there are some examples of photo-Fries rearrangements involving an intramolecular photochemical [1,3]-acyl migration from 1-acyl-3-alkylindoles to the corresponding 3-acylindolenines: Y. Ban, K. Yoshida. J. Goto, T. Oishi, and E. Takeda, Tetrahedron, 1983, 39, 3657.
23. (a) N. G. Anderson and R. G. Lawton, Tetrahedron Lett., 1977, 1843.
24. (b) For the construction of an eleven-membered ring lactam as a minor by-product, see reference 11c.
25. I. W. Southon and J. Buckingham, "Dictionary of Alkaloids", Chapman and Hall, London, 1989.