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Report | Regular issue | Vol 23, No. 4, 1985, pp.881-887
Published online, 1st January, 1970
DOI: 10.3987/R-1985-04-0881
The Chemistry of Drugs. VI. Thermal Decomposition of Qinghaosu

Xuan-De Luo,* Herman J. C. Yeh, Arnold Brossi, Judith L. Flippen-Anderson, and Richard Gilardi

*Laboratory of Chemistry, National Institute of Arthritis, Diabetes, and Digestive and Kidney Diseases, National Instituteof Health, Bethesda, Maryland 20205, U.S.A.

Abstract

Hearing qinghaosu in refluxing xylene for 22 h afforded decomposition products 2 and 4 in 15% yield each. Structures of 2 and 4 were assigned based on their 1H-NMR and 13C-NMR data and the former confirmed by a single crystal X-ray analysis. Structure 4, supported by spectral data and a successful O-acetylation of the OH group remains tentative. Structures 2 and 4 contain a newly formed tetrahydrofuran ring, originating by breakage of the original peroxide group.