Synthesis of Triazolo and Pyrazolo Derivatives of Quinoline Nucleus
Abstract
New heterocyclic derivatives of quinoline are reported. Reaction of quinoline-2-thiol 4 with hydrazine hydrate gave 2-hydrazionoquinoline 5. Treatment of 5 with CS2 in pyridine afforded 1,2,4-triazolo-[4,3-a]-quinolin-1-2H-thione 6, whereas the reaction of 5 with carboxylic acids namely formic acid or acetic acid, yielded the 1,2,4-triazol-[4,3-a]-quinolin 7 or 5-methyl-1,2,4-triazolo [4,3-a]-quinoline 8 through ring closure.
Diazotization of 5 under acidic conditions produced the fused tetrazole compound 9, tetrzolo-[1,5-a]-quinoline. Moreover, treatment of 5 with active methlyene compounds gave two pyrazole derivatives 10 and 11. Azomethines 12a-e were prepared through condensation of 5 with aromatic aldehydes or ketones.
Keyword: triazoloquinoline, tetrazoloquinoline, pyrazoloquinolines, azomethines.
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ISSN (Paper)2224-3224 ISSN (Online)2225-0956
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