2-(3-ETHYL-2,2-DIMETHYLCYCLOBUTYLMETHYL)-4(3H)-QUINAZOLINONES

Abstract

Anthranilic acid and its 5-bromo and 4-chloro derivatives react with pinanoic and pinonoic acid chlorides to give the corresponding N-acyl derivatives. The pinanoyl derivatives give the corresponding 2-(3-ethyl-2,2-dimethyl-cyclobutylmethyl)-4-(3H)-quinazolinones when refluxed in formamide. Pinanoylanthranilic acid reacts with dicyclohexylcarbodiimide to give 2-(3-ethyl-2,2-dimethyl-cyclobutylmethyl)benz-3,1-oxazin-4(H)-one and subsequently with hydrazine hydrate to give 3-amino-2-(3-ethyl-2,2-dimethylcyclobutylmethyl)-4(3H)-quinazolinone. Refluxing of the pinanoyl- and pinonoylanthranilic acids with acetic anhydride gives acetylanthranilic acid, and pinonoylanthranilic acid gives 4(3H)-quinazolinone with formamide.

Authors: F. M. Avotin'sh, M. V. Petrova, P. V. Pastors, and A. Ya. Strakov.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (6), pp 722-728

http://link.springer.com/article/10.1007/BF02251633