A novel intramolecular photocyclization of N-(2-bromoalkanoyl) derivatives of 2-acylanilines via 1,8-hydrogen abstraction

Helvetica Chimica Acta

Volumn 88, Issue 5, 2005, Pages 996-1003

  Nishio, Takehiko ^a   Koyama, Hiroyuki ^a   Sasaki, Daigo ^a   Sakamoto, Masami ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IRRADIATION; MOLECULAR DYNAMICS; NITROGEN COMPOUNDS;

BROMO-MIGRATION PRODUCTS; CYCLIZATION; DEHYDROBROMINATION; LACTAMS;

PHOTOCHEMICAL REACTIONS;

2 ACYLANILINE DERIVATIE; ANILIDE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; ENAMINE; HYDROGEN; LACTAM DERIVATIVE; N (2 ACYLPHENYL) 2 BROMO 2 METHYLPROPAMIDE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; ATOM; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; DEACYLATION; DEHYDROBROMINATION; IRRADIATION; PHOTOCHEMISTRY; PHOTOCYCLIZATION; PHOTOREACTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 20344364631     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590095     Document Type: Article

References (30)

1. P. J. Wagner, Acc. Chem. Res. 1971, 4, 168;
2. P. J. Wagner, Acc. Chem. Res. 1983, 16, 461;
3. P. J. Wagner, Acc. Chem. Res. 1989, 22, 83;
4. P. Wagner, in 'CRC Handbook of Organic Photochemistry and Photobiology', Eds. W. M. Horspool, P.-S. Song, CRC Press, New York, 1995, p. 449.
5. P. J. Wagner, B.-S. Park, in 'Organic Photochemistry', Ed. A. Padwa, Marcel Dekker, New York, 1991, Vol. 11, p. 227;
6. P. Wagner, P. Klan, in 'CRC Handbook of Organic Photochemistry and Photobiology', 2nd edn., Eds. W. M. Horspool, F. Lenci, CRC Press, Boca Raton, 2004, p. 52-1.
7. G. L. Descotes, in 'CRC Handbook of Organic Photochemistry and Photobiology', Eds. W. M. Horspool, P.-S. Song, CRC Press, New York, 1995, p. 501;
8. T. Nishio, Koukagaku [Photochemistry] 2003, 34, 2.
9. H. A. J. Carless, S. Mwesigye-Kibense, J. Chem. Soc., Chem. Commun. 1987, 1673.
10. G. Adam, A. Preiss, P. D. Hung, Tetrahedron 1987, 43, 5815.
11. F. Cottet, L. Cottier, G. Descotes, Can. J. Chem. 1990, 68, 1251.
12. G. A. Kraus, Y. Wu, J. Am. Chem. Soc. 1992, 114, 8705.
13. G. A. Kraus, W. Zhang, Y. Wu, Chem. Commun. 1996, 1439.
14. K. Mizuno, S. Konishi, Y. Yoshimi, A. Sugimoto, Chem. Commun. 1998, 1659.
15. R. Breslow, Acc. Chem. Res. 1980, 13, 170.
16. Y. Kanaoka, Acc. Chem. Res. 1978, 11, 407;
17. P. H. Mazzocchi, in ;Organic Photochemistry'; Ed. A. Padwa, Marcel Dekker, New York, 1981, p. 421;
18. J. D. Coyle, in 'Synthetic Organic Photochemistry'; Ed. W. M. Horspool, Plenum Press, New York, 1984, p. 259;
19. H. Mauder, A. G. Griesbeck, in 'CRC Handbook of Organic Photochemistry and Photobiology', Eds. W. M. Horspool, P.-S. Song, CRC Press, New York, 1995, p. 513.
20. T. Hasegawa, T. Ogawa, K. Miyata, A. Karakizawa, M. Komiyama, K. Nishizawa, M. Yoshioka, J. Chem. Soc., Perkin Trans. 1 1990, 901;
21. T. Hasegawa, Y. Yamazaki, M. Yoshioka, Trends Photochem. Photobiol. 1997, 4, 27.
22. S. Hu, D. C. Neckers, Tetrahedron 1997, 53, 7165;
23. S. Hu, D. C. Neckers, J. Org. Chem. 1997, 62, 7827.
24. T. Hasegawa, S. Kosaku, J. Ueno, S. Oguchi, Bull. Chem. Soc. Jpn. 1982, 55, 3659.
25. a) Y. Ogata, K. Takagi, I. Isibe, J. Org. Chem. 1971, 36, 3945;
26. b) G. R. Lenz, Synthesis 1978, 489;
27. c) I. Ninomiya, T. Naito, Heterocycles 1981, 15, 1433;
28. d) I. Ninomiya, T. Naito, Yuki Gosei Kagaku Kyokaishi 1989, 47, 916, and refs. cit. therein;
29. e) T. Nishio, H. Asai, T. Miyazaki, Helv. Chim. Acta 2000, 83, 1475.
30. T. Nishio, M. Tabata, H. Koyama, M. Sakamoto, Helv. Chim. Acta 2005, 88, 78.