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Reaction of 4-iodobenzoic acid or 4-iodobenzoyl chloride with n-alkylalcohol gave n-alkyl-4-iodobenzoate compounds in 83-92% yields. Mixed copper,znic benylic nucleophiles were prepared by n-alkyl-4-iodobenzoateswith znic metal insertion,followed by transmetalization with copper.Additionof these nucleophiles to N-acylpyridinium salts gave the intermediates,1,4- dihydropyridines.These intermediates which were temporarily stable underair at room temperature,could be oxidized by sulfur to produce n-alkyl-4-(4'-pryidyl)-benzoayes in 42-56% yields.
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