Dimerization of 2,5-dihydroxybenzoquinones in water

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 8, 1998, Pages 1129-1234

  Kiuchi, Fumiyuki ^a,b   Takashima, Hiromi ^a   Tsuda, Yoshisuke ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

1,4 dibenzofurandione; 2,5 dihyroxybenzoquinone; Dimerization; Furanylidene benzofuranone; X ray analysis

Indexed keywords

2,5 DIHYDROXY 3 METHYLBENZOQUINONE; 2,5 DIHYDROXYBENZOQUINONE DERIVATIVE; BENZOQUINONE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIMERIZATION; DRUG STRUCTURE; HEATING; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0031752965     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1229     Document Type: Article

References (11)

1. Kiuchi F., Suzuki N., Fukumoto Y., Goto Y., Mitsui M., Tsuda Y., Chem. Pharm. Bull., 46, 1225-1228 (1998).
2. a) Jägers E., Steglich W., Angew. Chem. Int. Ed. Engl., 20, 1016-1017 (1981);
3. b) Gill M., Steglich W., "Progress in the Chemistry of Organic Natural Products," Vol. 51. Springer-Verlag. Wien, 1987, pp. 98-109.
4. The authors thank Dr, A. Mühlbauer and Prof. W. Steglich for providing spectral data of bovilactone-4,4.
5. Longer treatment (30 min, room temperature) of 2a gave, instead of 5 and 6, three products, all of which had five OMe groups. Although spectral analyses of the products suggested ortho-ester structures, detailed structure determination will be the subject of a future publication.
6. Compounds 8a and 8b reversibly isomerized on silica gel plates, though only to a small extent, to 9a and 9b, respectively. However, 4a, 5, and 6 did not show such behavior on similar treatment. The reason for this isomerization is not clear at this moment.
7. Ueki Y., Itoh M., Katoh T., Terashima S., Tetrahedron Lett., 37, 5719-5722 (1996).
8. Carney J. R., Scheuer P. J., Tetrahedron Lett., 34, 3727-3730 (1993).
9. Steglich et al. proposed a different mechanism for formation of 2a through a ketene intermediate (see ref. 2). However, such reactive species is unlikely in an aqueous medium.
10. Tsuda Y., Nunozawa T., Nitta K., Yamamoto Y., Chem. Pharm. Bull., 28, 920-925 (1980).
11. All calculations were performed using the TEXSAN crystallo- graphic software package of Molecular Structure Corporation (1985).