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Molbank 2018, 2018(2), M997; https://doi.org/10.3390/M997

5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine

Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus
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Received: 13 May 2018 / Revised: 15 May 2018 / Accepted: 16 May 2018 / Published: 16 May 2018
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Abstract

Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N′-(perfluorophenyl)benzohydrazide (3) (37%). The X-ray crystallography of 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) is provided. Microwave irradiation (100 W) of perfluorophenylbenzohydrazide 3 with K2CO3 (1.1 equiv) in THF at ca. 120 °C (sealed tube, 80 PSI) for 3 h gives oxadiazine 5 (85%), while reduction of the nitro group using Sn (4 equiv) in glacial acetic acid at ca. 20 °C for 30 min, followed by cyclodehydration at ca. 118 °C for 20 min and treatment with 2 M NaOH for 24 h resulted in 1-(perfluorophenyl)-3-phenyl-1,2,4-benzotriazin-4-yl (4) with 93% yield. View Full-Text
Keywords: cyclisation; nucleophilic aromatic substitution; oxadiazine; halonitrobenzene; hydrazide; benzotriazine; organic radical cyclisation; nucleophilic aromatic substitution; oxadiazine; halonitrobenzene; hydrazide; benzotriazine; organic radical
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).

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Zissimou, G.A.; Kourtellaris, A.; Koutentis, P.A. 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine. Molbank 2018, 2018, M997.

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