Anand, Devireddy P. S. Patel, Om Maurya, Rahul K. Kant, Ruchir Yadav, Prem P. Substrate Controlled Synthesis of Benzisoxazole and Benzisothiazole Derivatives via PhI(OAc)<sub>2</sub>‑Mediated Oxidation Followed by Intramolecular Oxidative O–N/S–N Bond Formation A phenyliodine­(III) diacetate (PIDA)-mediated, highly efficient and tandem approach for the synthesis of aryldiazenylisoxazolo­(isothiazolo)­arenes from simple 2-amino-<i>N</i>′-arylbenzohydrazides has been developed. The reaction proceeds via formation of (<i>E</i>)-(2-aminoaryl)­(aryldiazenyl)­methanone as the key intermediate, followed by intramolecular oxidative O–N/S–N bond formation in one pot at room temperature. The quiet different reactivity of the substrate is due to the formation of a diazo intermediate which encounters a nucleophilic attack by carbonyl oxygen on the electrophilic amine to produce isoxazole products, as compared to the previous reports,, in which an <i>N</i>-acylnitrenium ion intermediate is intramolecularly trapped by an amine group. tandem approach;isoxazole products;Substrate Controlled Synthesis;Benzisothiazole Derivatives;nucleophilic attack;electrophilic amine;PIDA;reaction proceeds;formation;carbonyl oxygen;amine group;room temperature 2015-12-18
    https://acs.figshare.com/articles/dataset/Substrate_Controlled_Synthesis_of_Benzisoxazole_and_Benzisothiazole_Derivatives_via_PhI_OAc_sub_2_sub_Mediated_Oxidation_Followed_by_Intramolecular_Oxidative_O_N_S_N_Bond_Formation/2097412
10.1021/acs.joc.5b02276.s002