Abstract

Abstract The reaction of aromatic azines with diphenylcyclopropenone in refluxing toluene gave 5-aryl-2,3-diphenyl-2-pyrrolin-4-ones (4) in moderate yields via initial [2+3] 1:1 cycloaddition and subsequent elimination of an aromatic nitrile from the adducts. Treatment with phosphorus pentasulfide deoxygenated the compounds 4 to 5-aryl-2,3-diphenyl-pyrroles. The same compounds 4 were oxidized to 2-aryl-4,5-diphenyl-1,3-oxazin-6-ones (11) by refluxing the pyridine solution in a stream of oxygen, by treatment with hydrogen peroxide, or by irradiation of the chloroform solution in a stream of oxygen. Treatment with alkali in aqueous pyridine converted 4 into 3-aroylamino-2,3-diphenylacrylic acids. These were also obtained from the hydrolysis of 11. When p-dimethylaminobenzaldehyde azine reacted with diethyl azodicarboxylate in refluxing toluene, a 1:2 conjugated adduct, 3,6-bis(p-dimethylaminophenyl)-1,2,7,8-tetrakis(ethoxycarbonyl)-1,2,4,5,7,8-hexaaza-3,5-octadiene, and a 1:1 conjugate adduct, 3,6-bis p(-dimethylaminophenyl)-1,2-bis(ethoxycarbonyl)-1,2,4,5-tetraaza-3,5-hexadiene, were obtained.

Full Text
Paper version not known

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call