Synthesis of 1.2.3.4-tetrahydro-2.4-dioxoquinazoline derivatives for pharmacological study.
The condensation of 4-chloroanthranilic acid with several substituted monophenylureas is described. Reacting equimolecular amounts of the haloanthranilic acid with monophenylurea, p-tolylurea, p-methoxyphenylurea, p-ethoxyphenylurea, p-bromophenylurea, p-chlorophenylurea and m-chlorophenylurea--by fusion in a pressure bottle--yielded the corresponding 7-chloro-3-aryl-.2.3.4-tetrahydro-2.4-dioxoquinazoline (1a--g). On the other hand, o-substitute phenylureas, instead of affording the expected condensation products, yielded a compound which was shown to be 7-chlorobenzoyleneurea (2), the formation of which is accounted for.
D055598:Chemical Phenomena; D002621:Chemistry; D003500:Cyclization; D008722:Methods; D011799:Quinazolines / Q000138:chemical synthesis*; D062367:ortho-Aminobenzoates
D011799:Quinazolines; D062367:ortho-Aminobenzoates