Photoinduced molecular transformations. Part 159.1 formation of some furonaphthyridinones by selective β-scission of cyclobutanoxyl radicals generated from [2+2] photoadducts of 4-hydroxy-1-phenyl [1,8] naphthyridin-2(1H)-one with alkenes

Tetrahedron

Volumn 52, Issue 17, 1996, Pages 6125-6138

  Senboku, Hisanori ^a   Takashima, Megumi ^a   Suzuki, Masayoshi ^a   Kobayashi, Kazuhiro ^a   Suginome, Hiroshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 NAPHTHYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029868890     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00210-4     Document Type: Article

References (20)

1. Part 158. Onto, K.; Sasaki, T.; Suginome, H; J. Org. Chem.,1995, 60, 6208-6210.
2. For a review, see Suginome, H: Photochemistry of Alkyl Hypohalites. In Handbook of Organic Photochemistry and Photobiology; Horspool, W.H.; Song, P. -S. Eds.; CRC Press.: Boca Raton, FL., 1995;pp.1229-1253.
3. (a) Suginome, H.; Liu, C.F.; Seko, S.; Kobayashi, K.J. Org.Chem., 1988, 53, 5952-5959. (b) Suginome, H.; Kobayashi, K.; Itoh, M.; Seko, S.; Furusaki, A. J. Org.Chem.,1990, 55, 4933-4943. (c) Kobayashi, K.; Suzuki, M.; Suginome, H.J. Org. Chem., 1992, 57, 599-606. (d) Suginome, H.; Kajizuka, Y.; Suzuki, M.; Senboku, H.; Kobayashi, K. Heterocycles, 1994, 37, 283-288.
4. (a) Suginome, H.; Liu, C.F.; Seko, S.; Kobayashi, K.J. Org.Chem., 1988, 53, 5952-5959. (b) Suginome, H.; Kobayashi, K.; Itoh, M.; Seko, S.; Furusaki, A. J. Org.Chem.,1990, 55, 4933-4943. (c) Kobayashi, K.; Suzuki, M.; Suginome, H.J. Org. Chem., 1992, 57, 599-606. (d) Suginome, H.; Kajizuka, Y.; Suzuki, M.; Senboku, H.; Kobayashi, K. Heterocycles, 1994, 37, 283-288.
5. (a) Suginome, H.; Liu, C.F.; Seko, S.; Kobayashi, K.J. Org.Chem., 1988, 53, 5952-5959. (b) Suginome, H.; Kobayashi, K.; Itoh, M.; Seko, S.; Furusaki, A. J. Org.Chem.,1990, 55, 4933-4943. (c) Kobayashi, K.; Suzuki, M.; Suginome, H.J. Org. Chem., 1992, 57, 599-606. (d) Suginome, H.; Kajizuka, Y.; Suzuki, M.; Senboku, H.; Kobayashi, K. Heterocycles, 1994, 37, 283-288.
6. (a) Suginome, H.; Liu, C.F.; Seko, S.; Kobayashi, K.J. Org.Chem., 1988, 53, 5952-5959. (b) Suginome, H.; Kobayashi, K.; Itoh, M.; Seko, S.; Furusaki, A. J. Org.Chem.,1990, 55, 4933-4943. (c) Kobayashi, K.; Suzuki, M.; Suginome, H.J. Org. Chem., 1992, 57, 599-606. (d) Suginome, H.; Kajizuka, Y.; Suzuki, M.; Senboku, H.; Kobayashi, K. Heterocycles, 1994, 37, 283-288.
7. (a) Blythin, D.J.; Watkins, R.W. US.4680297. (Chem. Abstr., 1988, 108, 37817w). (b) Sherlock, M.H.; US.4596809. (Chem. Atar.,105,153050c). (c) Sherlock, M.H.; Smith, S.R.; Siegel, M.I. Eur. Pat. Appl. EP 196024. (Chem. Abstr.,1985, 102, 166726r). (e) Smith, S.R.; Siegel, M.I. PCT. Int. Appl. WO 9607537. (Chem. Abstr.,1987, 107,183554d). (f) Blythin, D.J. Eur.Pat. Appl. EP.144996. (Chem. Abstr.1985, 103, 215271v).
8. (a) Blythin, D.J.; Watkins, R.W. US.4680297. (Chem. Abstr., 1988, 108, 37817w). (b) Sherlock, M.H.; US.4596809. (Chem. Atar.,105,153050c). (c) Sherlock, M.H.; Smith, S.R.; Siegel, M.I. Eur. Pat. Appl. EP 196024. (Chem. Abstr.,1985, 102, 166726r). (e) Smith, S.R.; Siegel, M.I. PCT. Int. Appl. WO 9607537. (Chem. Abstr.,1987, 107,183554d). (f) Blythin, D.J. Eur.Pat. Appl. EP.144996. (Chem. Abstr.1985, 103, 215271v).
9. (a) Blythin, D.J.; Watkins, R.W. US.4680297. (Chem. Abstr., 1988, 108, 37817w). (b) Sherlock, M.H.; US.4596809. (Chem. Atar.,105,153050c). (c) Sherlock, M.H.; Smith, S.R.; Siegel, M.I. Eur. Pat. Appl. EP 196024. (Chem. Abstr.,1985, 102, 166726r). (e) Smith, S.R.; Siegel, M.I. PCT. Int. Appl. WO 9607537. (Chem. Abstr.,1987, 107,183554d). (f) Blythin, D.J. Eur.Pat. Appl. EP.144996. (Chem. Abstr.1985, 103, 215271v).
10. (a) Blythin, D.J.; Watkins, R.W. US.4680297. (Chem. Abstr., 1988, 108, 37817w). (b) Sherlock, M.H.; US.4596809. (Chem. Atar.,105,153050c). (c) Sherlock, M.H.; Smith, S.R.; Siegel, M.I. Eur. Pat. Appl. EP 196024. (Chem. Abstr.,1985, 102, 166726r). (e) Smith, S.R.; Siegel, M.I. PCT. Int. Appl. WO 9607537. (Chem. Abstr.,1987, 107,183554d). (f) Blythin, D.J. Eur.Pat. Appl. EP.144996. (Chem. Abstr.1985, 103, 215271v).
11. (a) Blythin, D.J.; Watkins, R.W. US.4680297. (Chem. Abstr., 1988, 108, 37817w). (b) Sherlock, M.H.; US.4596809. (Chem. Atar.,105,153050c). (c) Sherlock, M.H.; Smith, S.R.; Siegel, M.I. Eur. Pat. Appl. EP 196024. (Chem. Abstr.,1985, 102, 166726r). (e) Smith, S.R.; Siegel, M.I. PCT. Int. Appl. WO 9607537. (Chem. Abstr.,1987, 107,183554d). (f) Blythin, D.J. Eur.Pat. Appl. EP.144996. (Chem. Abstr.1985, 103, 215271v).
12. Sherlock, M.H.; Kaminski, J.J.; Tom, W.C.; Lee, J.F.; Wong, S. -C.; Kreutner, W.; Bryant, R.W.; McPhail. A.T., J. Med. Chem., 1988, 31, 2108-2121.
13. Wohl, R.T. Synthesis, 1974, 38-39.
14. Corey, E.J.; Bass, J.D.; LeMahieu, R.; Mitra, R.B. J. Am. Chem. Soc., 1964, 86, 5570-5583. Rubin, M.B.; Maymon, T.; Grover, D. Isr. J. Chem., 1970, 8, 717-730.
15. Corey, E.J.; Bass, J.D.; LeMahieu, R.; Mitra, R.B. J. Am. Chem. Soc., 1964, 86, 5570-5583. Rubin, M.B.; Maymon, T.; Grover, D. Isr. J. Chem., 1970, 8, 717-730.
16. For reviews, see (a) Baldwin, S.W: Synthetic Aspects of 2+2 Cycloadditions of α,β-Unsaturated Carbonyl Compounds. In Organic Photochemistry, Padwa, A: Ed.;Marcel Dekker.: New York, Vol.5, 1981, pp.123-225. (b) Weedon, A. C: Enone Photochemical Addition in Organic Synthesis. In Synthetic Organic Photochemistry ; Horspool, W M: Ed.; Plenum Press.: New York, 1984.; pp.61-143. (c) Schuster, D.I.; Lem, G.; Kaprinidis, N.A. Chem. Rev., 1993, 93, 3-22. (c) Schuster, D.I:. [2+2]-Photoadditions of Cyclohexenones to Alkenes. In Handbook of Organic Photochemistry and Photobiology ; Horspool, W.M.; Song,P.-S. Eds.; CRC Press, Boca Raton, FL., 1995; pp.652-669.
17. For reviews, see (a) Baldwin, S.W: Synthetic Aspects of 2+2 Cycloadditions of α,β-Unsaturated Carbonyl Compounds. In Organic Photochemistry, Padwa, A: Ed.;Marcel Dekker.: New York, Vol.5, 1981, pp.123-225. (b) Weedon, A. C: Enone Photochemical Addition in Organic Synthesis. In Synthetic Organic Photochemistry ; Horspool, W M: Ed.; Plenum Press.: New York, 1984.; pp.61-143. (c) Schuster, D.I.; Lem, G.; Kaprinidis, N.A. Chem. Rev., 1993, 93, 3-22. (c) Schuster, D.I:. [2+2]-Photoadditions of Cyclohexenones to Alkenes. In Handbook of Organic Photochemistry and Photobiology ; Horspool, W.M.; Song,P.-S. Eds.; CRC Press, Boca Raton, FL., 1995; pp.652-669.
18. For reviews, see (a) Baldwin, S.W: Synthetic Aspects of 2+2 Cycloadditions of α,β-Unsaturated Carbonyl Compounds. In Organic Photochemistry, Padwa, A: Ed.;Marcel Dekker.: New York, Vol.5, 1981, pp.123-225. (b) Weedon, A. C: Enone Photochemical Addition in Organic Synthesis. In Synthetic Organic Photochemistry ; Horspool, W M: Ed.; Plenum Press.: New York, 1984.; pp.61-143. (c) Schuster, D.I.; Lem, G.; Kaprinidis, N.A. Chem. Rev., 1993, 93, 3-22. (c) Schuster, D.I:. [2+2]-Photoadditions of Cyclohexenones to Alkenes. In Handbook of Organic Photochemistry and Photobiology ; Horspool, W.M.; Song,P.-S. Eds.; CRC Press, Boca Raton, FL., 1995; pp.652-669.
19. For reviews, see (a) Baldwin, S.W: Synthetic Aspects of 2+2 Cycloadditions of α,β-Unsaturated Carbonyl Compounds. In Organic Photochemistry, Padwa, A: Ed.;Marcel Dekker.: New York, Vol.5, 1981, pp.123-225. (b) Weedon, A. C: Enone Photochemical Addition in Organic Synthesis. In Synthetic Organic Photochemistry ; Horspool, W M: Ed.; Plenum Press.: New York, 1984.; pp.61-143. (c) Schuster, D.I.; Lem, G.; Kaprinidis, N.A. Chem. Rev., 1993, 93, 3-22. (c) Schuster, D.I:. [2+2]-Photoadditions of Cyclohexenones to Alkenes. In Handbook of Organic Photochemistry and Photobiology ; Horspool, W.M.; Song,P.-S. Eds.; CRC Press, Boca Raton, FL., 1995; pp.652-669.
20. Takahashi, H.; Itoh, M.; Suginome, H.; Masamune, T. Chem. Lett., 1979, 901-902.