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Paper | Regular issue | Vol 36, No. 5, 1993, pp.961-969
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6152
Synthesis of Organofluorine Compounds Utilizing 3-[1-(3-Fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl]quinoxalin-2(1H)-one as a Precursor

Nagwa Rashed,* Hamida Abdel Hamid, and Mahmoud Shoukry

*Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt


The reaction of D-erythro-2,3-hexodiulosono-1,4-lactone with 1,2-diaminobenzene followed by 3-fluorophenylhydrazine and the reaction of the product with dimethyl sulfate, sodium metaperiodate and acetic anhydride in pyridine have been investigated. The isopropylidenation of 3-[1-(3-fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl]quinoxalin-2(1H)-one under thermodynamic controlled conditions has been studied. Compounds 3-[1-(3-fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl]quinoxalin-2(1H)-one and its N-methyl derivative undergo dehydrative cyclisation in boiling acetic anhydride to the corresponding pyrazolylquinoxalinones.