A study on the ring transformation of dihydroisoxazolopyrimidine

Synthetic Communications

Volumn 27, Issue 19, 1997, Pages 3477-3484

  Kim, Jae Nyoung ^a   Lee, Hong Jung ^a   Kim, Hyoung Rae ^b   Ryu, Eung K ^b  

^a Chonnam National University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG DEGRADATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030773833     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708005650     Document Type: Article

References (10)

1. Kim, J. N. and Ryu, E. K., J. Org. Chem., 1992, 57, 1088.
2. Kim, J. N. and Ryu, E. K., Heterocycles, 1992, 34, 1423.
3. Fox, J. J., Praag, D. V., Wempen, I., Doerr, I. L., Cheong, L., Knoll, J. E., Eidinoff, M. L., Bendich, A. and Brown, G. B., J. Am. Chem. Soc., 1959, 81, 178.
4. Kim, J. N. and Ryu, E. K., J. Org. Chem., 1992, 57, 6649.
5. Similar ring-opening reaction pathways have been reported in dihydroazaxanthine system, see (a) Sasaki, T., Minamoto, K. and Suzuki, T., J. Org. Chem., 1976, 41, 1100. (b) Sasaki, T., Minamoto, K., Suzuki, T. and Sugiura, T., J. Am. Chem. Soc., 1978, 100, 2248. (c) Sasaki, T., Minamoto, K., Suzuki, T. and Yamashita, S., Tetrahedron, 1980, 36, 865.
6. Similar ring-opening reaction pathways have been reported in dihydroazaxanthine system, see (a) Sasaki, T., Minamoto, K. and Suzuki, T., J. Org. Chem., 1976, 41, 1100. (b) Sasaki, T., Minamoto, K., Suzuki, T. and Sugiura, T., J. Am. Chem. Soc., 1978, 100, 2248. (c) Sasaki, T., Minamoto, K., Suzuki, T. and Yamashita, S., Tetrahedron, 1980, 36, 865.
7. Similar ring-opening reaction pathways have been reported in dihydroazaxanthine system, see (a) Sasaki, T., Minamoto, K. and Suzuki, T., J. Org. Chem., 1976, 41, 1100. (b) Sasaki, T., Minamoto, K., Suzuki, T. and Sugiura, T., J. Am. Chem. Soc., 1978, 100, 2248. (c) Sasaki, T., Minamoto, K., Suzuki, T. and Yamashita, S., Tetrahedron, 1980, 36, 865.
8. The magnitude of the coupling constant (J = 9.5 Hz) is in good agreement with the magnitude of the cis coupling constant established for a series of 3-phenyl-2-isoxazolines. See: Sustmann, R., Huisgen, R. and Huber, H., Chem. Ber., 1967, 100, 1802.
9. Hansen, J. F., Kim, Y. I. and McCrotty, S. E., J. Heterocyclic Chem., 1980, 17, 475.
10. McKillop, A., Hunt, J. D., Naylor, R. D. and Taylor, E. C., J. Am. Chem. Soc., 1971, 93, 4918.