REACTIVITY OF 1,1-DISUBSTITUTED INDAZOL-3-YLIO OXIDES - SYNTHESIS OF SOME SUBSTITUTED INDAZOLOLS AND INDAZOLINONES

Some aspects of the reactivity of 1,1-disubstituted indazol-3-ylio oxides (indazolol-derived aminimides) have been studied. Treatment of these compounds with hydrochloric acid gave the corresponding indazolium salts which, through elimination of an alkyl chloride, afforded 1 -substituted indazol-3-ols. Treatment with alkoxides yielded N',N'-disubstituted 2-alkoxybenzohydrazides or 1-substituted indazolols (aryl or alkyl ether elimination products, respectively). The thermal rearrangements of indazolylio oxides gave 1-substituted indazolols, 1,2-disubstituted indazolinones and 3-alkoxy-1-alkylindazoles depending on the substituents. The direct cyclization of N',N'-disubstituted 2-chloro-5-nitrobenzohydrazides to indazole derivatives as well as the reactivity of some of the above mentioned compounds are also reported.