Collect. Czech. Chem. Commun. 1990, 55, 2967-2976

Synthesis of isomeric 1,1'-phenylene-bis(6-azauracil-5-carbonitriles)

Jan Slouka

Department of Analytical and Organic Chemistry, Palacký University, 771 46 Olomouc


The described synthesis of all three isomeric 1,1'-phenylene-bis(6-azauracil-5-carbonitriles) IVa-IVc starts from the respective 1-nitrophenyl-6-azauracil-5-carbonitriles Ia-Ic which were reduced to the corresponding amino derivatives IIa-IIc, diazotized, and coupled with ethyl cyanoacetylcarbamate to give the isomeric hydrazones IIIa-IIIc which were finally cyclized to the title compounds containing two 6-azauracil rings. A general formula is presented for calculation of mutual distance of arbitrary atoms in any planar molecules.