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Paper | Regular issue | Vol 38, No. 1, 1994, pp.57-69
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5873
Reactions of 5-(p-Anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d][1,3]oxazin-4-one

Hassan M. F. Madkour,* Mounir A. I. Salem, Taha M. Abdel-Rahman, and Mohamed E. Azab

*Laboratory of Synthetic Organic Chemistry, Chemistry Department, Faculty of Science, Ain Shams University, Abbassiya 11566, Cairo, Egypt

Abstract

5-(p-Anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d][1,3]oxazin-4-one (III) was prepared. The reactivity of III towards nucleophilic reagents was investigated. 5-(p-Anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d]pyrimidin-4-one(VI) was synthesised from III by the action of ammonium acetate and zinc chloride. The structure of VI was chemically confirmed by reactions with acetic anhydride, benzoyl chloride, chloroacetic acid, methyl iodide, dimethyl sulphate and ethyl bromoacetate. Compound (VI) reacted with secondary and primary amines under Mannich conditions to afford 5-(p-anisyl)-2-methyl-3-methylene substituted amino-7-(p-tolyl)-4H-pyrido[2,3-d]pyrimidin-4-ones (XIV) and (XV), respectively. Thiation of VI gave the thione 5-(p-anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d]pyrimidin-4-thiones(XIX).