A highly efficient and very mild one-pot synthesis of Nacylsulfonamides is described using cyanuric chloride. In this synthesis, structurally diverse carboxylic acids and sulfonamides are reacted in the presence of cyanuric chloride, triethylamine, and alumina in anhydrous acetonitrile at room temperature to afford various N-acylsulfonamides in excellent yields.
The click synthesis of some oxiconazole analogs 5a -5v having 1H-1,2,3-triazolyl residues by Huisgen cycloaddition was achieved in four steps (Scheme 1). Oximation of phenacyl chloride (1) followed by azidation of 2-chloro-1-phenylethanone oxime (2) provided azido ketoxime 3. The CuIcatalyzed Huisgen cycloaddition of 3 with terminal alkynes gave the 4-substituted (at the triazole) 2-(1H-1,2,3-triazol-1-yl)-1-phenylethanone oximes 4a -4i. The O-alkylation of 4a -4i with various alkyl halides resulted in the formation of the target molecules 5a -5v in good yields.Helvetica Chimica Acta -Vol. 94 (2011) Scheme 1. Synthesis of the 1H-1,2,3-Triazolyl-Based Oxiconazole Analogues 5a -5v Scheme 2. Terminal Alkynes from Propargyl Bromide and Nucleophiles
A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in refluxing N,N-dimethylformamide, furnishes the corresponding N-alkyl derivatives in good yields. This methodology is highly efficient for various structurally diverse primary alcohols and also useful for N-alkylation of other N-heterocycles containing an acidic N-H bond.
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