The aza-Michael addition reaction of 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-one/thione-5-ones to α,β-ethylenic compounds in the presence of KF/Al 2 O 3 furnishes N3-substituted quinazolinone derivatives. Those groups (NO 2 , MeO) with larger steric hindrance at the o-position of the phenyl ring of quinazolinone have an apparent affect on the chemical selectivity thus giving the N1-subsituted products.Scheme 1 Synthesis of N-substituted octahydroquinazoline-2-one/thione-5-ones 3 and 4.
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