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Paper | Regular issue | Vol 43, No. 6, 1996, pp.1201-1209
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7416
Synthesis and Basicity of 4-(N,N-Dimethylamino)-2-arylquinazolines

Wojciech Zielinski *, Agnieszka Kudelko, and Elizabeth M. Holt

*Institute of Organic Chemistry and Technology, Silesian Technical University, 44-101 Gliwice, Poland

Abstract

The reaction of substituted N-phenylbenzimidoyl chlorides with N,N-dimethylcyanamide in the presence of titanium tetrachloride has yielded seven 4-(N,N-dimethylamino)-2-arylquinazolines substituted on the phenyl ring with electron donating or withdrawing groups. pKa values have been determined for these compounds and analyzed in conjunction with the Hammett σ constants to observe the influence of these phenyl substituents upon the basicity of 4-(N,N-dimethylamino)-2-arylquinazolines. The ρ value, single crystal X-ray analysis and 15N-nmr spectra give evidence about the preferential site of protonation in such systems.