SYNTHESIS OF ANTICOCCIDIALS AND AMINOSUGARS FROM FURAN. STEREOCHEMICAL STUDIES OF THE NEW COMPOUNDS BY 1H NMR
Abstract
2H-PYRAN-3(6H)-ONE CARBAMIDE AND P-NO2-PHENYL-CARBONATE AND 5- PYRAN-[3,2-D]-OXAZ HAVE BEEN SYNTHESIZED WITH SEVERAL SUBSTITUENTS (AR-S-AR-, AR-SO2-AR, ACNH-AR-SO2-AR, BR-AR-). THEIR STEREOCHEMISTRY WAS STUDIED (A NEW KARPLUS-GARBIS IS PROPOSED) AS WELL AS THEIR ANTIMICROBIAL (1,5 GR/ML AGAINST STAPHYLOCOCCOUS) ANDANTICOCCIDIAL ACTIVITY (10PPM IN VITRO, 200PPM IN VIVO). THE SAME WAY WERE STUDIED THE MICHAEL TYPE PRODUCTS OF 2H-PYRAN-3(6H) -ONES WITH -N3, NH3 AND -S-AR-NH2 (DAPSONE ANALOGS). A NEW SYNTHESIS OF 2H-PYRAN-3(6H)-ONES FROM FURFURYL-ALCOHOLS IS PROPOSED BY THE USE OF NBS WHICH DO NOT OXIDIZE THE AR-S-AR- GROUP. THERE ARE ALSO SYNTHESIZED 1-O-ACETYL-2-AZIDO-2,3,6- TRIDEOXY-HEXOPYRANOZES FROM FURAN HAVING RIBO AND XYLO CONFIGURATION (1H NMR AND 13C NMR). THE MASS SPECTRAOF THE NEW PRODUCTS WERE ALSO STUDIED.
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