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Regioselective Fluorination of 7-Oxo-1,2,4-benzotriazines Using Selectfluor

School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland
Department of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, Cyprus
Author to whom correspondence should be addressed.
Present address: Department of Pharmacy, School of Life Sciences, Pharmacy and Chemistry, Kingston University, Penrhyn Road, Kingston upon Thames KT1 2EE, UK.
Molecules 2019, 24(2), 282;
Received: 18 December 2018 / Revised: 3 January 2019 / Accepted: 8 January 2019 / Published: 14 January 2019
(This article belongs to the Special Issue Recent Advances in Nitrogen-Containing Aromatic Heterocycles)
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). View Full-Text
Keywords: iminoquinone; enamine; fluorine; heterocyclic compound; microwave iminoquinone; enamine; fluorine; heterocyclic compound; microwave
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MDPI and ACS Style

Mirallai, S.I.; Koutentis, P.A.; Aldabbagh, F. Regioselective Fluorination of 7-Oxo-1,2,4-benzotriazines Using Selectfluor. Molecules 2019, 24, 282.

AMA Style

Mirallai SI, Koutentis PA, Aldabbagh F. Regioselective Fluorination of 7-Oxo-1,2,4-benzotriazines Using Selectfluor. Molecules. 2019; 24(2):282.

Chicago/Turabian Style

Mirallai, Styliana I., Panayiotis A. Koutentis, and Fawaz Aldabbagh. 2019. "Regioselective Fluorination of 7-Oxo-1,2,4-benzotriazines Using Selectfluor" Molecules 24, no. 2: 282.

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