Palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides to produce quinazolin-4(3H)-ones.
A wide variety of substituted quinazolin-4(3H)-ones were prepared in 63-91% yields by the palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides and carbon monoxide. The reaction is believed to proceed via in situ formation of an amidine, followed by oxidative addition, CO insertion, and intramolecular cyclization to give the substituted quinazolin-4(3H)-ones.
Zheng
Zhaoyan
Z
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Alper
Howard
H
D000578:Amidines / Q000138:chemical synthesis; D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000578:Amidines; D006843:Hydrocarbons, Chlorinated; D006847:Hydrocarbons, Iodinated; D052999:Quinazolinones; D010165:Palladium; D002248:Carbon Monoxide