K. Gewald, Osmar Calderon, H. Schäfer
Jul 12, 1984
Citations
0
Influential Citations
21
Citations
Journal
European Journal of Organic Chemistry
Abstract
Synthesis of 4-Aminocinnolines from (Arylhydrazono)(cyano)acetic Acid Derivatives The intramolecular Friedel-Crafts reaction of (arylhydrazono)(cyano)acetamides and -malono-nitriles 1 yields the 4-amino-3-cinnolinecarboxylic acid derivatives 2. Toluene as solvent takes part in the reaction of 1d and e and forms the 4-amino-3-cinnolyl p-tolyl ketones 3. Ethyl (phenylhydrazono)(cyano)acetate reacts in the presence of AlCl3 to yield the 4-hydroxy-3-cinnolinecarbonitrile (4). The pyrimido[5,4-c]cinnolinone 6, the 4-amino-3-cinnolinecarboxylic acid 2g, and its thioamide 2h can be obtained from 2.