Ceric ammonium nitrate (CAN) mediated novel dimerizations of 4-hydroxyquinolin-2(1H)-ones: the first example of reactions of oxygen-centered radicalsfrom 1,3-dicarbonyl compounds

Authors
Ye, JH Xue, J Ling, KQ Xu, JH
Citation
Jh. Ye et al., Ceric ammonium nitrate (CAN) mediated novel dimerizations of 4-hydroxyquinolin-2(1H)-ones: the first example of reactions of oxygen-centered radicalsfrom 1,3-dicarbonyl compounds, TETRAHEDR L, 40(7), 1999, pp. 1365-1368
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
7
Year of publication
1999
Pages
1365 - 1368
Database
ISI
SICI code
0040-4039(19990212)40:7<1365:CAN(MN>2.0.ZU;2-E
Abstract
Reactions of 4-hydroxyquinolin-2(1H)-ones (1) and 3-alkylated 4-hydroxyquin olin-2(1H)ones (2) with CAN in methanol gave quinolin-2(1H)-one dimers 3, 1 0 and 11 with C-C and C-O linkages between the two nitrogen containing sis- member rings, respectively, showing the ambident reactivities of alpha,alph a'-dicarbonylalkyl radicals as carbon- and oxygen-centered radicals. (C) 19 99 Elsevier Science Ltd. All rights reserved.