MAOS of Sugar Phenylosazones and their Derived Pyrazoles and Triazoles

Microwave‐assisted organic synthesis (MAOS) has proven to be practical to provide heterocycles from sugar osazones; an efficient method was developed for the characterization of sugars via their osazones 1–4 using microwave irradiation. The microwave‐assisted organic synthesis irradiation technique has been applied to convert d‐arabino‐hexose phenylosazone to 2‐phenyl‐4‐(d‐arabinotetrahydroxybutyl‐1,2,3‐triazole (5), which was then oxidized to the corresponding aldehyde whose oxime 9 was transformed to 4‐cyano‐2‐phenyltriazole 10. The condensation of 7 with thiosemicarbozide gave 10. Degradation of 1 afforded mesoxaldehyde 1,2‐bisphenylhydrazone 11, which cyclized to 1‐phenyl‐4‐phenylazo‐pyrazole (12) under acidic conditions. Irradiation of 6 in HBr/AcOH afforded 4‐(d‐arabino‐2′,3′‐di‐O‐acetyl‐1′,4′‐dibromobutyl)‐2‐phenyl‐2H‐1,2,3‐triazole. The acetylated phenylosazone was converted to furopyridazine 14. The irradiation of phenylosazone with acetic anhydride in pyridine gave the respective O‐acetyl derivative, whereas with boiling acetic anhydride gave the pyrazole 14, which afforded 15 and 16.