FACILE SYNTHESIS OF 2-SUBSTITUTED-QUINAZOLIN-4-(3H)-ONES PROMOTED BY SmI₂

Abstract

Mediated by SmI 2 , 2-substituted-quinazolin-4-(3H)-ones are readily accessible in fair yields by reaction of N,N-diethyl-onitrobenzamide with appropriate aryl and benzyl nitriles.

Quinoline, quinazoline and acridone alkaloids

“…Samarium() iodide in THF has been shown to mediate the reaction between N,N-diethyl-o-nitrobenzamide and various benzonitriles or phenylacetonitrile to yield 2-substituted quinazolin-4(3H)-ones in yields of 55-75%. 91 Among the products formed was the alkaloid glycosminine (glycophymine) 184. The reaction failed with acetonitrile.…”

Studies on Quinazolines. 11. Intramolecular Imidate-Amide Rearrangement of 2-Substituted 4-(ω-Chloroalkoxy)quinazoline Derivatives. 1,3 -O → N Shift of Chloroalkyl Groups via Cyclic 1,3-Azaoxonium Intermediates

“…There are numerous methods available for the synthesis of quinazolinones and their derivatives . Reports on solid-phase synthesis of related quinazolinones are an additional impetus to explore their multifaceted importance.…”