Preparation of p-benzoquinono[b]oxepines and their aromatic ring annulated derivatives

Heterocycles

Volumn 43, Issue 8, 1996, Pages 1601-1604

  Kakusawa, Naoki ^a   Inui, Kiyohiro ^a   Kurita, Jyoji ^a   Tsuchiya, Takashi ^a  

^a HOKURIKU UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0005649395     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7500     Document Type: Article

References (14)

1. a) D. R. Boyd, "Comprehensive Helerocyclic Chemistry", Vol. 7, ed. by A. R. Katritzky and C.W. Rees, Pergamon Press, Oxford, 1984, pp. 547-592.
2. b) T. Mukai, T. Kumagai, and Y. Yamashita, Heterocycles, 1981, 15, 1569.
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. C. W. Rees and D. E. West, J. Chem. Soc. (C), 1970, 583.
7. 3) δ: 186.6 (s, 6-C), 181.8 (s, 9-C), 145.7 (s, 9a-C), 130.8 (s, 5a-C), 143.0 (d, 2-C), 136.1 (d, 8-C), 135.9 (d, 7-C), 135.3 (d, 4-C), 125.6 (d, 5-C), 118.3 (d, 3-C). 2-Phenyl-p-benzoquinono[b]oxepine (7b) : 20% yield, mp 127-128 °C. 2-Methoxy-p-benzoquinono[b]oxepme(7c) : 15% yield, mp 101.5-103 °C.
8. The values of the chemical shifts of the ring protons of 1-benzoxepine are reported in ref. 2. [δ : 6.14 (2-H), 5.35 (3-H), 5.93 (4-H), 6.54 (5-H).]
9. H.·Hofmann and P. Hofmann, Liebigs Ann. Chem., 1975, 1571.
10. H. Hofmann and P. Hofmann, Liebigs Ann. Chem., 1977, 1597.
11. 14 : mp 184-186 °C ; 17 : mp 24O-242 °C ; 20 : mp 179-181 °C.
12. M. P. Cava, A. A. Deana, andK. Muth, J. Am. Chem. Soc., 1959, 81, 6458.
13. M. Chigr, H. Fillion, and A. Rougny, Tetrahedron Lett., 1988, 29, 5913.
14. We thank Dr. Fumiyuki Kiuchi and Prof. Yoshinori Tsuda, Kanazawa University, for performing X-ray crystallographic analysis.