Studies of some fused-ring heterocycles and 2,6-Diarylpyridine derivatives

Abstract

This work reported is divided into two parts: the first part deals with quinoxaline derivatives and includes the preparation and characterisation of novel linear tricyclic quinones 1,4-diazanthracen-9,10-diones, (54) and (55). The reaction of diazanaphthoquinones and 1-acetyl-1,3-butadiene are used to produce these quinones through the Diels-Alder reaction. In addition hexaazapentacyclic 5,6,7,12,13, 14-hexaazapentacene was prepared by the reaction ofbis(2-chloroquinoxalin-3-yl)sulfide with thioxamide and the reaction of the sulfide with amines was investigated. Two different approaches to 6,13-dibutyl-5,6,7,12,13,14-hexaazapentacene are given. Derivatives of the pentacyclic, 6-thia- 5,7,12,13,14-pentaazapentacene and the unsubstituted 6,13 -dihydro compound are described. The novel N-(2,5-dimethoxy-6-nitrophenyl)guanidine is used to obtain 3-amino-5,6-dimethoxy-1 ,2,4-benzotriazine-1-oxide and 4,7 -dimethoxy-1 ,2,3 -benzotriazole is shown to be second product. Second part of the work is concerned with the development of a preparative route to 2,6-diphenylpyridines substituted with different groups on the phenyl nuclei. Several approaches were attempted. Finally, success was achieved and a series of compounds having basic chains of different length on the phenyl groups was prepared. One chain in each case had a terminal primary amine. The binding constants of the primary amines and their N-acetyl derivatives with DNA were determined using fluorescence spectroscopy.