Thermal addition reaction of aroylketenes with cyclic enol ethers

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 7, 1996, Pages 1298-1304

  Saithoh, Toshiaki ^a   Oyama, Taichi ^a   Horiguchi, Yoshie ^a   Toda, Jun ^a   Sano, Takehiro ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

4 pyrone; aroylketene; cyclic enol ether; thermal addition reaction

Indexed keywords

ALKENE DERIVATIVE; ETHER DERIVATIVE; FURAN DERIVATIVE; KETENE DERIVATIVE; KETONE DERIVATIVE; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOSPECIFICITY; THERMAL EXPOSURE;

EID: 0030056549     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1298     Document Type: Article

References (11)

1. For a review, see: Sato M., Yuki Gosei Kagaku Kyokai Shi. 46, 596 (1988); Wentrup C., Heilmayer W., Kollenz G., Synthesis, 1994, 1219.
2. For a review, see: Sato M., Yuki Gosei Kagaku Kyokai Shi. 46, 596 (1988); Wentrup C., Heilmayer W., Kollenz G., Synthesis, 1994, 1219.
3. Wenkert C., Ananthanarayan T. P., Ferreira V. F., Hoffman M. G., Hong S. K., J. Org. Chem., 55, 4975-4976 (1990); Kolensnikova O. N., Livantsova L. I., Shurov S. N., Zaitseva G. S., Andreichikov Yu. S., Zh. Obshch. Khim., 60. 467-468 (1990); Shurov S. N., Livantsova L. I., Zaitseva G. S., Kolensnikova O. N., Andreichikov Yu. S., ibid., 62, 227-228 (1992).
4. Wenkert C., Ananthanarayan T. P., Ferreira V. F., Hoffman M. G., Hong S. K., J. Org. Chem., 55, 4975-4976 (1990); Kolensnikova O. N., Livantsova L. I., Shurov S. N., Zaitseva G. S., Andreichikov Yu. S., Zh. Obshch. Khim., 60. 467-468 (1990); Shurov S. N., Livantsova L. I., Zaitseva G. S., Kolensnikova O. N., Andreichikov Yu. S., ibid., 62, 227-228 (1992).
5. Wenkert C., Ananthanarayan T. P., Ferreira V. F., Hoffman M. G., Hong S. K., J. Org. Chem., 55, 4975-4976 (1990); Kolensnikova O. N., Livantsova L. I., Shurov S. N., Zaitseva G. S., Andreichikov Yu. S., Zh. Obshch. Khim., 60. 467-468 (1990); Shurov S. N., Livantsova L. I., Zaitseva G. S., Kolensnikova O. N., Andreichikov Yu. S., ibid., 62, 227-228 (1992).
6. Sano T., Saithoh T., Toda J.. Heterocycles, 36, 2139 (1993).
7. Saithoh T., Oyama T., Sakurai K., Niimura Y., Hinata M., Horiguchi Y., Toda J., Sano T., Chem. Pharm. Bull., 44. 956-966 (1996).
8. Molecular mechanics calculations (MM2) were performed by Chem 3D plus ver. 3.0.1 for Apple Macintosh.
9. For the synthesis of 4-pyrone derivatives by Diels-Alder reaction of aldehydes with active dienes, see: Bednarski M. D., Lyssikatos J. K., "Comprehensive Organic Synthesis," Vol. 2, ed. by Trost B. M., Pergamon Press, Oxford, 1991, pp. 661-706.
10. Cazeau P., Dubaudin F., Moulines F., Babot O., Dunogues J., Tetrahedron, 43, 2075 (1987).
11. Murai S., Hasegawa K., Sonoda N., Angew. Chem., Int. Ed. Engl., 14, 636 (1975).