چكيده فارسي :
The cleavage of a C-O bond of ethers is a versatile and nearly ubiquitous transformation in organic synthesis for the production of many pharmaceuticals and other fine chemicals. In this connection, a variety of reagents and methods in which are capable of cleaving ethers have been developed[1].Among them, the most conventional method involving acylative cleavage of ethers with acyl chlorides is one of the attractive methods for the preparation of esters. Thus, it is of great interest in the development of the convenient and practical catalytic methods for the transformation of ethers into esters. There are some reports on the acylative cleavage of ethers with acyl chlorides using Lewis acids. However, these methods involved some disadvantages, such as the use of harsh, toxic, expensive, unstable reagents or catalysts, drastic conditions, and low yields of products. Cyanuric chloride (2, 4, 6-trichloro [1, 3, 5]-triazine) (CC or TCT) is a stable, non-volatile, inexpensive and a safe reagent which has long been used in various organic transformations [2].In recent years, we developed the application of CCin various organic transformations as a useful reagent for the synthesis of sulfonamides from amine-derived sulfonate salt, One-Pot synthesis of N-acyl sulfonamides,synthesis of ynones, andalso One-Pot regioselective N-acylation of nucleobases [3].Encouraged by the intense research activities in the field of ethers‘ C-O bond cleavage and also in pursuit of our ongoing interest in utilizing cyanuric chloride in organic transformation; hereby, we disclose cyanuric chloride as an efficient reagent for ring opening of cyclic ethers (ether bond cleavage) via carboxylic acids(Scheme 1). To this end, diverse activated carboxylic acids by CC were used to react with cyclic ethers using catalytic amount of MgCl2 in anhydrous MeCN at reflux condition. The influence of parameters on this protocol including the type of solvent, base and temperature were assessed. Good to excellent yields of chloroalkylesters were obtained exploitingthis current approach.
