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Article

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

1
School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland
2
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; https://doi.org/10.3390/molecules24020282
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. https://doi.org/10.3390/molecules24020282

AMA Style

Mirallai SI, Koutentis PA, Aldabbagh F. Regioselective Fluorination of 7-Oxo-1,2,4-benzotriazines Using Selectfluor. Molecules. 2019; 24(2):282. https://doi.org/10.3390/molecules24020282

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. https://doi.org/10.3390/molecules24020282

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