Synthesis of some novel pyrazolo and triazolo quinolines from coumarin compounds

Abstract EN

Coumadin and its furor derivatives (psoralene and isopsoralene) are used as precursor for preparation of heterocyclic compounds.

The 4-methyl-7-mthoxycoumarin, psoralene and substituted isopsoralene (II, III and IV) which are derived from 4-methyl-7-hydroxycoumarin (I), when reacted with hydrazine hydrate through nucleophile substitution reaction under basic condition give N-amino-2-quinolone and its furo derivatives (1, 5 and 9) in good yields Reaction of these compounds (1, 5 and 9) with methyl acetoacetate, ethyl acetoimidate or thiosemicarbazide, a new heterocyclic compounds will be formed pyrazolo-quinoline and it is furo derivatives (2,6 and 10) ; 1, 2, 4-triazolo-quinoline and its furo derivatives (3, 7 and 11) and 1, 2, 4- triazolo-quinoline-2-thione (4, 8 and 12) respectively.

The assigned structure of the prepared compounds were elucidated by the available physical and spectral methods IR, UV and 1H-NMR.