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 oxi des (indazolol-derived aminimides) have been studied. Treatment of the se compounds with hydrochloric acid gave the corresponding indazolium salts which, through elimination of an alkyl chloride, afforded 1 -sub stituted indazol-3-ols. Treatment with alkoxides yielded N',N'-disubst ituted 2-alkoxybenzohydrazides or 1-substituted indazolols (aryl or al kyl ether elimination products, respectively). The thermal rearrangeme nts of indazolylio oxides gave 1-substituted indazolols, 1,2-disubstit uted indazolinones and 3-alkoxy-1-alkylindazoles depending on the subs tituents. The direct cyclization of N',N'-disubstituted 2-chloro-5-nit robenzohydrazides to indazole derivatives as well as the reactivity of some of the above mentioned compounds are also reported.