5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine
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...
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MDPI AG
2018-05-01
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| Series: | Molbank |
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| Online Access: | http://www.mdpi.com/1422-8599/2018/2/M997 |
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| author | Georgia A. Zissimou Andreas Kourtellaris Panayiotis A. Koutentis |
| author_facet | Georgia A. Zissimou Andreas Kourtellaris Panayiotis A. Koutentis |
| author_sort | Georgia A. Zissimou |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-14T02:48:54Z |
| format | Article |
| id | doaj.art-4dc3cb848863485d83ce6a5ea3913a1e |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-04-14T02:48:54Z |
| publishDate | 2018-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-4dc3cb848863485d83ce6a5ea3913a1e2022-12-22T02:16:23ZengMDPI AGMolbank1422-85992018-05-0120182M99710.3390/M997M9975,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazineGeorgia A. Zissimou0Andreas Kourtellaris1Panayiotis A. Koutentis2Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, CyprusDepartment of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, CyprusDepartment of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, CyprusTreating 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.http://www.mdpi.com/1422-8599/2018/2/M997cyclisationnucleophilic aromatic substitutionoxadiazinehalonitrobenzenehydrazidebenzotriazineorganic radical |
| spellingShingle | Georgia A. Zissimou Andreas Kourtellaris Panayiotis A. Koutentis 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine Molbank cyclisation nucleophilic aromatic substitution oxadiazine halonitrobenzene hydrazide benzotriazine organic radical |
| title | 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine |
| title_full | 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine |
| title_fullStr | 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine |
| title_full_unstemmed | 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine |
| title_short | 5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine |
| title_sort | 5 6 7 8 tetrafluoro 1 2 nitrophenyl 3 phenyl 1h benzo e 1 3 4 oxadiazine |
| topic | cyclisation nucleophilic aromatic substitution oxadiazine halonitrobenzene hydrazide benzotriazine organic radical |
| url | http://www.mdpi.com/1422-8599/2018/2/M997 |
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