Synthesis of quinoxalines by cyclization of alpha-arylimino oximes of alpha-dicarbonyl compounds

Authors
Xekoukoulotakis, NP Hadjiantoniou-Maroulis, CP Maroulis, AJ
Citation
Np. Xekoukoulotakis et al., Synthesis of quinoxalines by cyclization of alpha-arylimino oximes of alpha-dicarbonyl compounds, TETRAHEDR L, 41(52), 2000, pp. 10299-10302
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
52
Year of publication
2000
Pages
10299 - 10302
Database
ISI
SICI code
0040-4039(200012)41:52<10299:SOQBCO>2.0.ZU;2-Z
Abstract
Heating the title compounds 1 at reflux in acetic anhydride yields quinoxal ines 3 and 4 via a presumed aryliminoiminyl radical 5, resulting from homol ytic cleavage of the N-O bond in the intermediate ester 2. The observed reg ioselectivity of the reaction is also rationalized by implicating such a ra dical. (C) 2000 Elsevier Science Ltd. All rights reserved.