N- vs O-alkylation in 2(1H)-quinolinone derivatives

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 6999-7002

  Guo, Zhao Xia ^a   Cammidge, Andrew N ^a   McKillop, Alexander ^a   Horwell, David C ^b  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Alkylation; Phase transfer; Quinolinones

Indexed keywords

BENZYL CHLORIDE; BROMINE DERIVATIVE; FUSED CARBON NITROGEN OXYGEN HETEROCYCLE; HYDROXYL GROUP; NITROGEN; OXYGEN;

ALKYLATION; ARTICLE; CHEMICAL REACTION; LIQUID; PHASE TRANSITION; REACTION ANALYSIS; SOLID; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033578818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01422-7     Document Type: Article

References (12)

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5. 2: C 76.48%, H 5.21%, N 5.57%; found C 76.48%, H 5.07%, N 5.51%.
6. (a) Hopkins, G.; Jonak, J.P.; Minnemeyer, H.J. and Tieckelmann, H. J. Org. Chem., 1967, 32, 4040-4044.
7. (b) Dou, H.J.M.; Hassanaly, P. and Metzger, J. J. Heterocydic. Chem., 1977, 14, 321-323.
8. (c) Comins, D.L. and Jianhua, G. Tetrahedron Lett., 1994, 35, 2819-2822.
9. Gallo, R.J.; Makosza, M.; Dou, H.J.M. and Hassanaly, P. Adv. Heterocydic Chem., 1984, 36, 175-234 (and references therein).
10. 3: C 77.61%, H 5.7%, N 3.77%; found C 77.46%, H 5.71%, N 3.7%.
11. Control experiments were performed to ensure that the product distribution was not influenced by further equilibration (including Chapman rearrangement) under the reaction conditions.
12. 1H NMR spectroscopy of the oil indicated that 2 and 3 were the only products present in a ratio of 1:3.6.