Unambiguous structure elucidation of the reaction products of 3-acyl-4-methoxy-1-methylquinolinones with hydroxylamine via NMR spectroscopy
作者： Stefano Chimichi , Marco Boccalini , Alessandra Matteucci
DOI: 10.1016/J.TET.2007.08.108
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摘要: Abstract Reaction of 3-acyl-4-methoxy-1-methylquinolinones 2a,b with hydroxylamine has been investigated under different experimental conditions. Whereas compound 2a gives rise selectively and exclusively to the regioisomeric isoxazolo[4,5-c]- or isoxazolo[4,3-c]quinolin-4(5H)one (compound 3a 4a, respectively), reaction 2b always led a mixture required isoxazole together oxazole derivative. Structural elucidation all products independently achieved by multinuclear (13C 15N) magnetic resonance spectroscopy.
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sci-hub.se 参考文章(8)
Stefan A. Laufer, Simona Margutti, Martina D. Fritz, Substituted isoxazoles as potent inhibitors of p38 MAP kinase. ChemMedChem. ,vol. 1, pp. 197- 207 ,(2006) , 10.1002/CMDC.200500025
Thomas Kappe, Barbara Schnell, SYNTHESIS AND REACTIONS OF 3-AROYL DERIVATIVES OF 4-HYDROXY-2-QUINOLONES AND 4-HYDROXYCOUMARIN Journal of Heterocyclic Chemistry. ,vol. 33, pp. 663- 670 ,(1996) , 10.1002/JHET.5570330324
Waltraud Steinschifter, Werner Fiala, Wolfgang Stadlbauer, Synthesis of oxazolo[4,5‐c]quinolones by thermolytic degradation of 4‐azido‐2(1H)‐quinolones Journal of Heterocyclic Chemistry. ,vol. 31, pp. 1647- 1652 ,(1994) , 10.1002/JHET.5570310662
Stefano Chimichi, Marco Boccalini, Mohamed M.M. Hassan, Giampietro Viola, Francesco Dall'Acqua, Massimo Curini, Synthesis, structural determination and photo-antiproliferative activity of new 3-pyrazolyl or -isoxazolyl substituted 4-hydroxy-2(1H)-quinolinones Tetrahedron. ,vol. 62, pp. 90- 96 ,(2006) , 10.1016/J.TET.2005.09.135
Bryan H. Norman, Joseph M. Gruber, Sean P. Hollinshead, Joseph W. Wilson, James J. Starling, Kevin L. Law, Tracy D. Self, Linda B. Tabas, Daniel C. Williams, Donald C. Paul, Margaret M. Wagner, Anne H. Dantzig, Tricyclic isoxazoles are novel inhibitors of the multidrug resistance protein (MRP1) Bioorganic & Medicinal Chemistry Letters. ,vol. 12, pp. 883- 886 ,(2002) , 10.1016/S0960-894X(02)00051-3
Bryan H. Norman, Peter A. Lander, Joseph M. Gruber, Julian S. Kroin, Jeffrey D. Cohen, Louis N. Jungheim, James J. Starling, Kevin L. Law, Tracy D. Self, Linda B. Tabas, Daniel C. Williams, Donald C. Paul, Anne H. Dantzig, Cyclohexyl-linked tricyclic isoxazoles are potent and selective modulators of the multidrug resistance protein (MRP1) Bioorganic & Medicinal Chemistry Letters. ,vol. 15, pp. 5526- 5530 ,(2005) , 10.1016/J.BMCL.2005.08.075
Thomas KAPPE, Rudolf AIGNER, Monika JÖBSTL, Peter HOHENGASSNER, Wolfgang STADLBAUER, REACTIONS OF 3-ACYL-4-HYDROXY-2(1H)-QUINOLONES WITH NITROGEN BASES Heterocyclic Communications. ,vol. 1, pp. 341- 352 ,(1995) , 10.1515/HC.1995.1.5-6.341
Susumu Takada, Takashi Sasatani, Nobuo Chomei, Makoto Adachi, Toshio Fujishita, Masami Eigyo, Shunji Murata, Kazuo Kawasaki, Akira Matsushita, Synthesis and Structure−Activity Relationships of Fused Imidazopyridines: A New Series of Benzodiazepine Receptor Ligands Journal of Medicinal Chemistry. ,vol. 39, pp. 2844- 2851 ,(1996) , 10.1021/JM9600609