A CONVENIENT SYNTHESIS OF OTHERWISE INACCESSIBLE 3-AMINOCINNOLINE-4-CARBOXYLIC ACID-DERIVATIVES

Citation
M. Scobie et G. Tennant, A CONVENIENT SYNTHESIS OF OTHERWISE INACCESSIBLE 3-AMINOCINNOLINE-4-CARBOXYLIC ACID-DERIVATIVES, Journal of the Chemical Society, Chemical Communications, (21), 1994, pp. 2451-2452
Citations number
11
Categorie Soggetti
Chemistry
ISSN journal
00224936
Issue
21
Year of publication
1994
Pages
2451 - 2452
Database
ISI
SICI code
0022-4936(1994):21<2451:ACSOOI>2.0.ZU;2-B
Abstract
3-Amino-4-(2-nitroaryl)-2H-isoxazolin-5-ones, readily available by the sodium ethoxide catalysed cyclisation of amidoximes derived from ethy l 2-cyano-2-(2-nitroaryl)acetates, ring-close in the presence of sodiu m hydride to afford high yields of isoxazolo[3,4-c]cinnolin-1 (3H)-one 5-N-oxides; hydrazine effects the chemoselective reductive scission o f the isoxazoline ring in these heterocycles allowing simple and effic ient synthetic access to erstwhile unavailable 3-aminocinnoline-4-carb oxylic acid 1-N-oxides.