Generation of 6-(trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the application to synthesis of some fused nitrogen heterocycles carrying a trifluoromethyl group on the bridgehead position via radical cyclization of dihydropyridones

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8826-8830

  Okano, Takashi ^a,b   Sakaida, Tsutomu ^a,b   Eguchi, Shoji ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b Faculty of Engineering   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE; PYRIDONE DERIVATIVE; QUINOLIZINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030458584     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961030g     Document Type: Article

References (38)

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4. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
5. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
6. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
7. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
8. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
9. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
10. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
11. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
12. 5-Membered-ring-nitrogen heterocycles: (a) Abdul-Ghani, M. M.; Tipping, A. E. J. Fluorine Chem. 1995, 73, 189. (b) Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457. (c) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1994, 67, 183. (d) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749. (e) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (f) Bouillon, J. P.; Ates, C.; Janousek, Z.; Viehe, H. G. Tetrahedron Lett. 1993, 34, 5075. (g) Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. (h) Meazza, G.; Zanardi, G.; Piccardi, P. J. Heterocycl. Chem. 1993, 30, 365. (i) Okano, T.; Uekawa, T.; Morishima, N.; Eguchi, S. J. Org. Chem. 1991, 56, 5259.
13. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
14. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
15. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
16. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
17. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
18. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
19. 6-Membered-ring-nitrogen heterocycles: (a) Eguchi, S.; Umada, A.; Okano, T. Heterocycles 1996, 40, 333. (b) Atkinson, R. S.; Coogan, P. M.; Cornell, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 157. (c) Bouillon, J. P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. Ibid. 1995, 2907. (d) Yamamoto, M.; Burton, D. J.; Swenson, D. C. J. Fluorine Chem. 1995, 72, 49. (e) Baumann, L.; Folkerts, A.; Imming, P.; Klindert, T.; Massa, W.; Steitz, G.; Wocadlo, S. Liebigs Ann. 1995, 661. (f) Kobayashi, M.; Uneyama, K.; Hamada, N.; Kashino, S. Tetrahedron Lett. 1994, 35, 5235. (g) Bouillon, J. P.; Wynants, C.; Janousek, Z.; Viehe, H. G. Heterocycles 1994, 37, 915.
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33. For reviews on free radicals in organic synthesis: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. (b) Jasperse, C. P.; Curran, D. P. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. Synlett 1991, 63; (d) Synthesis 1988, 417 and 489. (e) Ramaiah, M. Tetrahedron 1987, 43, 3541.
34. For reviews on free radicals in organic synthesis: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. (b) Jasperse, C. P.; Curran, D. P. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. Synlett 1991, 63; (d) Synthesis 1988, 417 and 489. (e) Ramaiah, M. Tetrahedron 1987, 43, 3541.
35. For reviews on free radicals in organic synthesis: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. (b) Jasperse, C. P.; Curran, D. P. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. Synlett 1991, 63; (d) Synthesis 1988, 417 and 489. (e) Ramaiah, M. Tetrahedron 1987, 43, 3541.
36. For reviews on free radicals in organic synthesis: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. (b) Jasperse, C. P.; Curran, D. P. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. Synlett 1991, 63; (d) Synthesis 1988, 417 and 489. (e) Ramaiah, M. Tetrahedron 1987, 43, 3541.
37. 6-exo-Cyclization of 6-heptenyl radical is 100 times as slow as 5-exo cyclization of 5-hexenyl radical: Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 152.
38. Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4965.