Regioselective fluorination of 7-oxo-1,2,4-benzotriazines using selectfluor

Mirallai, Styliana I., Koutentis, Panayiotis A. and Aldabbagh, Fawaz (2019) Regioselective fluorination of 7-oxo-1,2,4-benzotriazines using selectfluor. Molecules, 24(2), p. 282. ISSN (online) 1420-3049


7-Oxo-1,2,4-benzotriazines (benzo[1,2,4]triazin-7-ones) are reversible thioredoxin reductase inhibitors that exhibit very strong correlations to pleurotin. In this article, we provide the first synthesis of fluorinated derivatives. Fluorination using Selectfluor of benzo[1,2,4]triazin-7-ones occurs regioselectively and in high yield at the enamine-activated position. This electron N-lone pair activation overrides the activation/deactivation effects of some other substituents. The reaction time was significantly reduced with the use of microwave irradiation at 120 °C and 7 bar. The cytotoxicity and cyclic voltammetry measurements for 8-fluoro-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one (2) are presented and compared with its synthetic precursor, 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one (1a).

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