Studies on the Reactions of Cyclic Oxalyl Compounds: Synthesis and Thermolysis of 2,3-Dihydro-4-(4-methylbenzoyl)-5-(4-methylphenyl)-furan-2,3-dione and its N-Reaction with Nucleophiles

Oxalyl chloride combines with 1,3-bis(4-methylphenyl) propane-1,3-dione to afford novel titled compound furan-2,3-dione 1, whose synthesis, x-ray structure analysis and some reaction are reported. thermolysis is supposed to occur by the ring opening of the compound 1 followed by the intermediate diacylketene dimerization resulting in the pyran-4-one 2. the reaction of 1 with some aromatic amines and diamines led to the formation of the pyrole-2’3-dione 3,4 and the quinxalin-2-one derivative 5, respectively. most of them were compared with their previous analogs. the structure of all products were confirmed by ir, 1h- and 13c-nmr spectroscopic measurements, in the case of 1 also by an x-rays study. 1 crystallizes in the monoclinic space group c2/c with eight molecules 1 per cell. the reaction pathways leading to the compounds 1,2 and 4 were briefly discussed.