- Frontier Orbital Interactions in the Regioselectivity of the Amination of Nitroquinolines by Liquid Ammonia/Potassium Permanganate
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5-Nitro-,6-nitro-,7-nitro-,8-nitro-,and 2-nitroquinoline and 5,7-dinitro and 6,8-dinitroquinoline were aminated in a liquid ammonia solution of potassium permanganate. 8-Nitro and 2-nitroquinoline were found to be unreactive.The intermediary ?-adducts,formed between 5,7-dinitro- and 6,8-dinitroquinoline and liquid ammonia, could be detected by 1H NMR spectroscopy.FMO calculations nicely confirm the experimentally observed regioselectivity of the amination.
- Wozniak, Marian,Baranski, Andrzej,Nowak, Krystyna,Plas, Henk C. van der
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- Bismuth nitrate as a source of nitro radical in ipso-nitration of carboxylic acids
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Aromatic nitro compounds are extensively used in synthetic chemistry. We disclose a new approach to obtain nitroarenes regioselectively starting from carboxylic acids under acid-free reaction conditions.
- Agasti, Soumitra,Maiti, Siddhartha,Maity, Soham,Anniyappan,Talawar,Maiti, Debabrata
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p. 120 - 124
(2019/05/22)
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- 3-cyanoquinoline derivatives
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A compound of the formula I STR1 where A is nitro, amino, halocarbonyl or halosulfonyl, R is hydrogen, halogen, nitro, cyano, C1 -C4 -alkanoylamino, hydroxyl, C1 -C4 -alkoxy phenoxy which is unsubstituted by methyl or chloro, mercapto, C1 -C4 -alkylthio, phenylthio which is unsubstituted or substituted by ethyl, fluoro, or methoxy, carboxyl, C1 -C4 -alkoxycarbonyl, phenoxycarbonyl which is unsubstituted or substituted by isopropyl, bromo, or methoxy, carbamoyl, hydroxysulfonyl, C1 -C4 -alkylsulfonyl, phenylsulfonyl which is unsubstituted or substituted by ethyl, chloro, or isopropoxy, sulfamoyl or trifluoromethyl or is C1 -C4 -alkyl which may be substituted by hydroxyl, C1 -C4 -alkoxy or halogen, and X and Y are each, independently of one another, halogen, hydroxysulfonyl, C1 -C4 -alkoxy or phenoxy which is unsubstituted or substituted by methyl or chloro, phenoxy, subject to the proviso that at least one of X and Y is halogen.
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