Facile Synthesis of Benzotriazines and Indoles by Ring-Scissions of α-Benzotriazol-1-yl Hydrazones

Alan R. Katritzky Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA

Jin Wang Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA

Nazira Karodia Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA

Jianqing Li Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA

Abstract

Abstract: α-(Benzotriazol-1-yl)hydrazones 2a-d and 13a-c were prepared by refluxing the corresponding α-(benzotriazol-1-yl)ketones with p-tosyl hydrazide or benzenesulfonyl hydrazide. Treatment of 2a-b with n-butyllithium in the presence of TMEDA gave benzotriazines 6a-b, while lithiation of 13a-c resulted in indole derivatives 16a-c, depending on the structure of the hydrazones.

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Facile Synthesis of Benzotriazines and Indoles by Ring-Scissions of α-Benzotriazol-1-yl Hydrazones

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Facile Synthesis of Benzotriazines and Indoles by Ring-Scissions of α-Benzotriazol-1-yl Hydrazones

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