Reaction of 1,2,4-triazine 1-oxides with benzyne : Formation of 1,3-benzoxazepine and 1,3,5,6-benzoxatriazonine derivatives

Heterocycles

Volumn 43, Issue 10, 1996, Pages 2091-2094

  Kakusawa, Naoki ^a   Sakamoto, Kazunori ^a   Kurita, Jyoji ^a   Tsuchiya, Takashi ^a  

^a HOKURIKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001576856     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7552     Document Type: Article

References (16)

1. R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 565, 633 ; B. Stanovinik, Tetrahedron, 1991, 47, 2925.
2. R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 565, 633 ; B. Stanovinik, Tetrahedron, 1991, 47, 2925.
3. H. Igeta, H. Arai, H. Hasegawa, and T. Tsuchiya, Chem. Pharm. Bull., 1975, 23, 2791.
4. J. Kurita, N. Kakusawa, S. Yasuike, and T. Tsuchiya, Heterocycles, 1990, 31, 1937.
5. N. Kakusawa, M. Imamura, J. Kurita, and T. Tsuchiya, Heterocycles, 1994, 38, 957.
6. G. G. Spence, E. C. Taylor, and O. Buchardt, Chem. Rev., 1970, 70, 231 ; F. Bellamy and J. Streith, Heterocycles, 1976, 4, 1391 ; A. Albini and M. Alpegiani, Chem. Rev., 1984, 84, 43.
7. G. G. Spence, E. C. Taylor, and O. Buchardt, Chem. Rev., 1970, 70, 231 ; F. Bellamy and J. Streith, Heterocycles, 1976, 4, 1391 ; A. Albini and M. Alpegiani, Chem. Rev., 1984, 84, 43.
8. G. G. Spence, E. C. Taylor, and O. Buchardt, Chem. Rev., 1970, 70, 231 ; F. Bellamy and J. Streith, Heterocycles, 1976, 4, 1391 ; A. Albini and M. Alpegiani, Chem. Rev., 1984, 84, 43.
9. J. Kurita, T. Iwata, S. Yasuike, and T. Tsuchiya, J. Chem. Soc., Chem. Commun., 1992, 81.
10. Compounds (5a,b) were obtained by m-chloroperbenzoic acid oxidation of the corresponding 3-phenyl-1,2,4-triazines [M. O'Rourke, S. A. Lang, Jr., and E. Cohen, J. Med. Chem., 1977, 20, 723]. Details about this oxidation will be described in a full paper.
11. O. Buchardt, C. Lohse, A. M. Duffield, and C. Djerassi, Tetrahedron Lett., 1967, 2741.
12. Satisfactory elemental analyses and spectroscopic data were obtained for all new compounds reported. 10a : Yellow needles, mp 185-187°C ; 10b : yellow needles, mp 228-230°C ; 10c : colorless needles, mp 116-118°C ; 10d : yellow needles, mp 165-167°C ; 10e : yellow needles, mp 172-173 °C.
13. W. W. Paudler and T. K. Chen, J. Org. Chem., 1971, 36, 787.
14. 3) δ : 156.1 (s, 3-C), 148.9 (s, 5a-C), 130.0 (d, 9-C), 129.3 (s, 9a-C), 124.7 (d, 7-C), 121.7 (d, 8-C), 110.4 (d, 6-C), 94.1 (s, 4a-C), 74.6 (s, 9b-C), 54.9 (q, 3-MeO), 24.2 and 21.2 (q, 9b- and 4a-Me).
15. 3) δ : 158.0 (s, 4-C), 155.1 (s, 2-C), 146.6 (s, 7-C), 146.3 (s, 11a-C), 130.6 (s, 7a-C), 129.8 (d, 8-C), 127.4 (d, 10-C), 125.9 (d, 9-C), 120.7 (d, 11-C), 54.0 (q, 4-MeO), 23.3 (q, 7-Me), 22.3 (q, 2-Me).
16. We thank Dr. Fumiyuki Kiuchi and Prof. Yoshinori Tsuda, Kanazawa University, for performing X-ray crystallographic analysis. Detail X-ray crystallographic data for the nine-membered ring (16) will be published in a full paper.