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
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.