Next Article in Journal
Pharmacokinetics, Tissue Distribution, Plasma Protein Binding Studies of 10-Dehydroxyl-12-Demethoxy-Conophylline, a Novel Anti-Tumor Candidate, in Rats
Previous Article in Journal
Elucidation of Vasodilation Response and Structure Activity Relationships of N2,N4-Disubstituted Quinazoline 2,4-Diamines in a Rat Pulmonary Artery Model
Previous Article in Special Issue
Synthesis and Antifungal Potential of Some Novel Benzimidazole-1,3,4-Oxadiazole Compounds
Article Menu
Issue 2 (January-2) cover image

Export Article

Open AccessFeature PaperArticle
Molecules 2019, 24(2), 282; https://doi.org/10.3390/molecules24020282

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
Present address: Department of Pharmacy, School of Life Sciences, Pharmacy and Chemistry, Kingston University, Penrhyn Road, Kingston upon Thames KT1 2EE, UK.
*
Author to whom correspondence should be addressed.
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)
Full-Text   |   PDF [2171 KB, uploaded 14 January 2019]   |  

Abstract

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
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top