1,2-Dihydroquinolin-2-one (carbostyril) anions as bidentate nucleophiles in their reactions with aryllead triacetates: Synthesis of 1-aryl- and 3-aryl-tetrahydroquinoline-2,5,8-triones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1997, Pages 229-233

  López Alvarado, Pilar ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748533856     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605139a     Document Type: Article

References (39)

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6. Some synthetic approaches: (a) G. R. Pettit, W. C. Fleming and K. D. Paull, J. Org. Chem., 1968, 33, 1089;
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30. Some non-functionalized aromatic systems have been oxidized to quinones by treatment with cerium ammonium sulfate (M. Periasamy and V. Bhatt, Synthesis, 1977, 330). However, several attempts to oxidize carbostyril by this method were unsuccessful.
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35. 5 may contribute to a certain preference for arylation on carbon rather than on nitrogen, a 'harder' nucleophile.
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38. (c) T. Moreno, M. Fernández, E. de la Cuesta and C. Avendaño, Heterocycles, 1996, 43, 817.
39. A similar difference in chemical shifts for both carbonyls has been described for other o- and p-quinones: W. Breitmaier and W. Woelter, Carbon-13 NMR Spectroscopy, 3rd edn., VCH, 1987, p. 222.