Synthesis and applications of [1-15N]-labeled 4,6-dimethyl-4H-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxide as a useful tool for mechanistic investigations

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6670-6675

  Sako, Magoichi ^a   Yaekura, Isamu ^a   Oda, Souichi ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4,6 DIMETHYL 4H [1,2,5]OXADIAZOLO[3,4 D]PYRIMIDINE 5,7 DIONE 1 OXIDE; 8 PHENYLTHEOPHYLLINE; NITRIC ACID; NITROGEN 15; PTERIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; NITRATION; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ANILINE COMPOUNDS; BENZYLAMINES; CYCLIC N-OXIDES; CYSTEAMINE; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; NITRIC OXIDE; NITROGEN ISOTOPES; PIPERIDINES; PYRIMIDINES; PYRIMIDINONES;

EID: 0034613384     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000835s     Document Type: Article

References (68)

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42. Krasnov, K. A. Russ. J. Org. Chem. 1998, 34, 115-119; Taylor, E. C.; Sowinski, F.; Yee, T. T.; Yoneda, F. J. Am. Chem. Soc. 1967, 89, 3369-3370. For other preparative methods of the unlabeled 4: Choy, N.; Russell, K. C. Heterocycles 1999, 51, 13-16. Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Heterocycles 1981, 15, 285-288. Senda, S.; Hirota, K.; Suzuki, M.; Takahashi, M. Chem. Pharm. Bull. 1977, 25, 563-568. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem. Soc., Perkin Trans. 1 1976, 2398-2402. Senda, S.; Hirota, K.; Takahashi, M. Heterocycles 1976, 4, 461-465. Yoneda, F.; Matsumoto, S.; Sakuma, Y.; Fukazawa, S. J. Chem. Soc., Perkin Trans. 1 1975, 1907-1909. Yoneda, F.; Fukazawa, S. J. Chem. Soc., Chem. Commun. 1972, 503-504. Nishigaki, S.; Fukazawa, S.; Ogiwara, K.; Yoneda, F. Chem. Pharm. Bull. 1971, 19, 206-207.
43. Krasnov, K. A. Russ. J. Org. Chem. 1998, 34, 115-119; Taylor, E. C.; Sowinski, F.; Yee, T. T.; Yoneda, F. J. Am. Chem. Soc. 1967, 89, 3369-3370. For other preparative methods of the unlabeled 4: Choy, N.; Russell, K. C. Heterocycles 1999, 51, 13-16. Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Heterocycles 1981, 15, 285-288. Senda, S.; Hirota, K.; Suzuki, M.; Takahashi, M. Chem. Pharm. Bull. 1977, 25, 563-568. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem. Soc., Perkin Trans. 1 1976, 2398-2402. Senda, S.; Hirota, K.; Takahashi, M. Heterocycles 1976, 4, 461-465. Yoneda, F.; Matsumoto, S.; Sakuma, Y.; Fukazawa, S. J. Chem. Soc., Perkin Trans. 1 1975, 1907-1909. Yoneda, F.; Fukazawa, S. J. Chem. Soc., Chem. Commun. 1972, 503-504. Nishigaki, S.; Fukazawa, S.; Ogiwara, K.; Yoneda, F. Chem. Pharm. Bull. 1971, 19, 206-207.
44. Krasnov, K. A. Russ. J. Org. Chem. 1998, 34, 115-119; Taylor, E. C.; Sowinski, F.; Yee, T. T.; Yoneda, F. J. Am. Chem. Soc. 1967, 89, 3369-3370. For other preparative methods of the unlabeled 4: Choy, N.; Russell, K. C. Heterocycles 1999, 51, 13-16. Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Heterocycles 1981, 15, 285-288. Senda, S.; Hirota, K.; Suzuki, M.; Takahashi, M. Chem. Pharm. Bull. 1977, 25, 563-568. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem. Soc., Perkin Trans. 1 1976, 2398-2402. Senda, S.; Hirota, K.; Takahashi, M. Heterocycles 1976, 4, 461-465. Yoneda, F.; Matsumoto, S.; Sakuma, Y.; Fukazawa, S. J. Chem. Soc., Perkin Trans. 1 1975, 1907-1909. Yoneda, F.; Fukazawa, S. J. Chem. Soc., Chem. Commun. 1972, 503-504. Nishigaki, S.; Fukazawa, S.; Ogiwara, K.; Yoneda, F. Chem. Pharm. Bull. 1971, 19, 206-207.
45. Krasnov, K. A. Russ. J. Org. Chem. 1998, 34, 115-119; Taylor, E. C.; Sowinski, F.; Yee, T. T.; Yoneda, F. J. Am. Chem. Soc. 1967, 89, 3369-3370. For other preparative methods of the unlabeled 4: Choy, N.; Russell, K. C. Heterocycles 1999, 51, 13-16. Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Heterocycles 1981, 15, 285-288. Senda, S.; Hirota, K.; Suzuki, M.; Takahashi, M. Chem. Pharm. Bull. 1977, 25, 563-568. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem. Soc., Perkin Trans. 1 1976, 2398-2402. Senda, S.; Hirota, K.; Takahashi, M. Heterocycles 1976, 4, 461-465. Yoneda, F.; Matsumoto, S.; Sakuma, Y.; Fukazawa, S. J. Chem. Soc., Perkin Trans. 1 1975, 1907-1909. Yoneda, F.; Fukazawa, S. J. Chem. Soc., Chem. Commun. 1972, 503-504. Nishigaki, S.; Fukazawa, S.; Ogiwara, K.; Yoneda, F. Chem. Pharm. Bull. 1971, 19, 206-207.
46. Krasnov, K. A. Russ. J. Org. Chem. 1998, 34, 115-119; Taylor, E. C.; Sowinski, F.; Yee, T. T.; Yoneda, F. J. Am. Chem. Soc. 1967, 89, 3369-3370. For other preparative methods of the unlabeled 4: Choy, N.; Russell, K. C. Heterocycles 1999, 51, 13-16. Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Heterocycles 1981, 15, 285-288. Senda, S.; Hirota, K.; Suzuki, M.; Takahashi, M. Chem. Pharm. Bull. 1977, 25, 563-568. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem. Soc., Perkin Trans. 1 1976, 2398-2402. Senda, S.; Hirota, K.; Takahashi, M. Heterocycles 1976, 4, 461-465. Yoneda, F.; Matsumoto, S.; Sakuma, Y.; Fukazawa, S. J. Chem. Soc., Perkin Trans. 1 1975, 1907-1909. Yoneda, F.; Fukazawa, S. J. Chem. Soc., Chem. Commun. 1972, 503-504. Nishigaki, S.; Fukazawa, S.; Ogiwara, K.; Yoneda, F. Chem. Pharm. Bull. 1971, 19, 206-207.
47. Krasnov, K. A. Russ. J. Org. Chem. 1998, 34, 115-119; Taylor, E. C.; Sowinski, F.; Yee, T. T.; Yoneda, F. J. Am. Chem. Soc. 1967, 89, 3369-3370. For other preparative methods of the unlabeled 4: Choy, N.; Russell, K. C. Heterocycles 1999, 51, 13-16. Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Heterocycles 1981, 15, 285-288. Senda, S.; Hirota, K.; Suzuki, M.; Takahashi, M. Chem. Pharm. Bull. 1977, 25, 563-568. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem. Soc., Perkin Trans. 1 1976, 2398-2402. Senda, S.; Hirota, K.; Takahashi, M. Heterocycles 1976, 4, 461-465. Yoneda, F.; Matsumoto, S.; Sakuma, Y.; Fukazawa, S. J. Chem. Soc., Perkin Trans. 1 1975, 1907-1909. Yoneda, F.; Fukazawa, S. J. Chem. Soc., Chem. Commun. 1972, 503-504. Nishigaki, S.; Fukazawa, S.; Ogiwara, K.; Yoneda, F. Chem. Pharm. Bull. 1971, 19, 206-207.
48. Maki, Y.; Sako, M.; Taylor, E. C. Tetrahedron Lett. 1971, 4271-4274. For other preparative methods of 5: (a) Reference 10a.
49. (b) Okamoto, Y.; Amemiya, H.; Kinoshita, T.; Shirai, M.; Matsumoto, Y. Polyhedron 1985, 4, 629-632. Okamoto, Y.; Ogura, K.; Kurasawa, Y.; Kinoshita, T. Heterocycles 1984, 22, 1231-1234.
50. (b) Okamoto, Y.; Amemiya, H.; Kinoshita, T.; Shirai, M.; Matsumoto, Y. Polyhedron 1985, 4, 629-632. Okamoto, Y.; Ogura, K.; Kurasawa, Y.; Kinoshita, T. Heterocycles 1984, 22, 1231-1234.
51. c) Yoneda, F.; Nishigaki, S. Chem. Pharm. Bull. 1971, 19, 1060-1062.
52. (d) Hirota, K.; Maruhashi, K.; Asao, T.; Senda, S. Chem. Pharm. Bull. 1982, 30, 3377-3379.
53. (e) Reference 1.
54. (f) Mineo, S.; Ogura, H.; Nakagawa, K. Chem. Pharm. Bull. 1980, 28, 2835-2838. Sakaguchi, M.; Miyata, Y.; Ogura, H.; Gonda, K.; Koga, S.; Okamoto, T. Chem. Pharm. Bull. 1979, 27, 1094-1100. Ogura, H.; Sakaguchi, M.; Okamoto, T.; Gonda, K.; Koga, S. Heterocycles 1979, 12, 359-363.
55. (f) Mineo, S.; Ogura, H.; Nakagawa, K. Chem. Pharm. Bull. 1980, 28, 2835-2838. Sakaguchi, M.; Miyata, Y.; Ogura, H.; Gonda, K.; Koga, S.; Okamoto, T. Chem. Pharm. Bull. 1979, 27, 1094-1100. Ogura, H.; Sakaguchi, M.; Okamoto, T.; Gonda, K.; Koga, S. Heterocycles 1979, 12, 359-363.
56. (f) Mineo, S.; Ogura, H.; Nakagawa, K. Chem. Pharm. Bull. 1980, 28, 2835-2838. Sakaguchi, M.; Miyata, Y.; Ogura, H.; Gonda, K.; Koga, S.; Okamoto, T. Chem. Pharm. Bull. 1979, 27, 1094-1100. Ogura, H.; Sakaguchi, M.; Okamoto, T.; Gonda, K.; Koga, S. Heterocycles 1979, 12, 359-363.
57. (g) Yoneda, F.; Senga, K.; Nishigaki, S. Chem. Pharm. Bull. 1973, 21, 260-263 and 1972, 20, 2063-2064.
58. (g) Yoneda, F.; Senga, K.; Nishigaki, S. Chem. Pharm. Bull. 1973, 21, 260-263 and 1972, 20, 2063-2064.
59. (h) Reference 3.
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61. Romerosa, A.; Colacio, E.; Suarez-Varela, J.; Avila-Roson, J. C.; Hidalgo, M. A.; Romero-Garzon, J. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, 51, 1005-1007. Orlov, V. D.; Kolos, N. N.; Tueni, M.; Yur'eva, E. Y.; Ivkov, S. M. Khim. Geterotsikl. Soedin 1992, 947-954. Pfleiderer, W.; Schundehutte, K.-H.; Ferch, H. Liebigs Ann. Chem. 1958, 615, 57-59. Taylor, E. C.; Loux, H. M.; Falco, E. A.; Hitchings, G. H. J. Am. Chem. Soc. 1955, 77, 2243-2248.
62. Romerosa, A.; Colacio, E.; Suarez-Varela, J.; Avila-Roson, J. C.; Hidalgo, M. A.; Romero-Garzon, J. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, 51, 1005-1007. Orlov, V. D.; Kolos, N. N.; Tueni, M.; Yur'eva, E. Y.; Ivkov, S. M. Khim. Geterotsikl. Soedin 1992, 947-954. Pfleiderer, W.; Schundehutte, K.-H.; Ferch, H. Liebigs Ann. Chem. 1958, 615, 57-59. Taylor, E. C.; Loux, H. M.; Falco, E. A.; Hitchings, G. H. J. Am. Chem. Soc. 1955, 77, 2243-2248.
63. Romerosa, A.; Colacio, E.; Suarez-Varela, J.; Avila-Roson, J. C.; Hidalgo, M. A.; Romero-Garzon, J. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, 51, 1005-1007. Orlov, V. D.; Kolos, N. N.; Tueni, M.; Yur'eva, E. Y.; Ivkov, S. M. Khim. Geterotsikl. Soedin 1992, 947-954. Pfleiderer, W.; Schundehutte, K.-H.; Ferch, H. Liebigs Ann. Chem. 1958, 615, 57-59. Taylor, E. C.; Loux, H. M.; Falco, E. A.; Hitchings, G. H. J. Am. Chem. Soc. 1955, 77, 2243-2248.
64. Ramm, M.; Schulz, B.; Thurner, J. U.; Ulbricht, M. Cryst. Res. Technol. 1990, 25, 297-303. Pozharskii, A. F.; Kuz'menko, V. V.; Nanavyan, I. M. Khim. Geterotsikl. Soedin. 1983, 1564. Kokel, B.; Viehe, H. G. Angew. Chem., Int. Ed. 1980, 19, 716-717.
65. Ramm, M.; Schulz, B.; Thurner, J. U.; Ulbricht, M. Cryst. Res. Technol. 1990, 25, 297-303. Pozharskii, A. F.; Kuz'menko, V. V.; Nanavyan, I. M. Khim. Geterotsikl. Soedin. 1983, 1564. Kokel, B.; Viehe, H. G. Angew. Chem., Int. Ed. 1980, 19, 716-717.
66. Ramm, M.; Schulz, B.; Thurner, J. U.; Ulbricht, M. Cryst. Res. Technol. 1990, 25, 297-303. Pozharskii, A. F.; Kuz'menko, V. V.; Nanavyan, I. M. Khim. Geterotsikl. Soedin. 1983, 1564. Kokel, B.; Viehe, H. G. Angew. Chem., Int. Ed. 1980, 19, 716-717.
67. 13C NMR spectral data (see the Experimental Section) of this product, however, suggested the occurrence of a redox reaction between the N-oxide 1 and piperidine leading to the oxadiazolopyrimidinedione 2 and the oxygenated piperidine (and subsequent nitrosation).
68. Uppu, R. M.; Pryor, W. A. J. Am. Chem. Soc. 1999, 121, 9738-9739.