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Abstract A mixture of quinazolin-4-ol (1) and thionyl chloride was refluxed followed by treating with sodium azide in dry DMF to afford 2 was formed in 95% yield (Scheme 1). Triphenyl phosphine and azide derivative 2 were dissolved in pyridine and kept at room temperature for 1 h to afford 3 in 98% (Scheme 1). The phosphinimine 3 in pyridine and concentrated ammonium hydroxide afforded the corresponding amine 4 in 80% (Scheme 1). A solution of 4, diethyl malonate, diethyl 2-methylmalonate, diethyl 2- ethylmalonate, diethyl 2-butylmalonate, and/or diethyl 2-phenylmalonate, and diphenyl ether were refluxed for 1 h. Diethyl ether was added with strong stirring and the products were collected by filtration to afford 5-9 in 53-72% yields (Scheme 2). |