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Molbank, Vol. 2018, Article M997: 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine

Molbank, Vol. 2018, Article M997: 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine

Molbank doi: 10.3390/M997

Authors: Georgia Zissimou Andreas Kourtellaris Panayiotis Koutentis

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.

Authors:   Zissimou, Georgia A.; Kourtellaris, Andreas ; Koutentis, Panayiotis A.
Journal:   Molbank
Volume:   2018
edition:   2
Year:   2018
Pages:   M997
DOI:   10.3390/M997
Publication date:   16-May-2018
Facts, background information, dossiers
  • nitrobenzene
  • Georgia
  • crystallography
More about Molecular Diversity Preservation International
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