Preparation method and application of 3-(substituted phenyl) oxetane-3-carboxylic acid and intermediate thereof
The preparation method comprises the following steps: taking 3-oxetanone (compound II) as an initial raw material, and carrying out Wittig reaction on the initial raw material and triethyl phosphonotriacetate under an alkaline condition to obtain a compound III; carrying out coupling reaction on the compound III and a boric acid compound IV to obtain a compound V; reducing the ester group of the compound V to generate a compound VI; carrying out nucleophilic substitution reaction on hydroxyl of the compound VI and sulfonyl chloride/sulfonic anhydride to generate a compound VII; reacting hydroxyl of the compound VI with a halogenating reagent to generate a compound VIII; carrying out elimination reaction on the compound VII or the compound VIII to generate a compound IX; and finally, oxidizing the double bonds of the compound IX to generate 3-(substituted phenyl) oxetane-3-carboxylic acid (compound I). The method is easy and convenient to operate and high in yield, the total yield can reach 35%, and large-scale production can be achieved.
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(2020/11/12)
Short Synthesis of Oxetane and Azetidine 3-Aryl-3-carboxylic Acid Derivatives by Selective Furan Oxidative Cleavage
Four-membered rings remain underexplored motifs despite offering attractive physicochemical properties for medicinal chemistry. Arylacetic acids bearing oxetanes, azetidines, and cyclobutanes are prepared in two steps: a catalytic Friedel-Crafts reaction from four-membered ring alcohol substrates, followed by mild oxidative cleavage. The suitability of the products as building blocks is reflected in their facile purification and amenability to derivatization. Examples include heteroaromatics and aryltriflates, as well as oxetane-derived profen drug analogues and a new endomorphin derivative containing an azetidine amino acid residue.
Bull, James A.,Choi, Chulho,Dubois, Maryne A. J.,Lee Wei Jie, Alvin,Mousseau, James J.,Smith, Milo A.,White, Andrew J. P.
supporting information
p. 5279 - 5283
(2020/08/14)
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