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Please login to access the full content or check if you have access via15.4.1 Product Subclass 1: Quinolin-2(1H)-ones
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Larsen, R. D., Science of Synthesis, (2005) 15, 551.
One of the first syntheses of a compound of the quinoline class was that of quinolin-2-one, reported in 1852. The product was prepared by reductive cyclization of 2-nitrocinnamic acid [(2E)-3-(2-nitrophenyl)acrylic acid], a method that is still commonly used.[1] The quinolin-2-ones [quinolin-2(1H)-ones] are also commonly referred to as carbostyrils, 2-hydroxyquinolines, 2-quinolinols, or 2-oxoquinolines. Quinolin-2-ones have two tautomeric forms, the lactam form 1 and the phenolic form 2 (Scheme 1).[19] In the solid state, the compound exists predominately as the lactam 1.[20,21] The IR spectra of quinolin-2-ones in solution are generally difficult to obtain because of their low solubility in most IR spectroscopy solvents; however, by using a mixture of chloroform and dimethyl sulfoxide, good solubility has been achieved and quite intense amide carbonyl bands were observed, indicating that the amide tautomer predominates.[22] Other studies have also indicated that the amide form predominates.[23] Comparison of the UV spectra of quinolin-2-one, 2-methoxyquinoline, and 1-methylquinolinone confirmed that the lactam form 1 indeed predominates in solution.[4]
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References
[1] | Meeeee, M. M., Meee. Mee., (8888) 88, 888. |
[4] | Meeeeeee, M., Me Meee'e Meeeeeeee ee Meeeee Meeeeeeee, 8ee ee., Meeeee, M., Me.; Meeeeeee: Meeeeeeee, (8888); Mee. 8-M, ee 888–888. |
[19] | Meeeeee, M. M.; MeMeeeee, M., Me Meeeeeeeeeeee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M.; Meee, M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 8. |
[20] | Meeeee, M.; Meeeeeee, M. M., M. Meee. Mee., (8888), 8888. |
[21] | Meeee, M. M., M. Meee. Mee., (8888), 8888. |
[22] | MeMeeeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
[23] | Meeeeeeee, M. M.; Meeeeeee, M. M., Mee. Meeeeeeeee. Meee., (8888) 8, 888. |
[24] | Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M., MMM; Meeeee, M., M. Mee. Meee., (8888) 88, 888. |
[25] | Meeeeeee, M. M.; Meeeee, M.; Meeee, M.; Meeeeee, M. M., Meeeeeeeeeee, (8888) 8, 888. |
[26] | Meeeeee, M. M., Mee. Meee. Mee., (8888) 88, 888. |
[27] | Meeeeee, M. M., Mee. Meee. Mee., (8888) 88, 888. |
[28] | Meeeeee, M. M., Mee. Meee. Mee., (8888) 88, 888. |
[29] | Meeeeee, M. M., Mee. Meee. Mee., (8888) 88, 888. |
[30] | Mee Meeee Meeee, 88ee Me., M'Meee, M. M.; Meeee, M.; Meeeeeeee, M. M.; Meeeeeeee, M. M., Me.; Meeeeeeee, M. M.; M'Meeeee, M. M.; Meeeeeee, M., Mee.; Meeee&Me. Mee.: Meeeeeeeee Meeeeee, MM, (8888); e 8888. |