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Three different synthetic routes were developed to introduce carbamoyloxy functional groups at the upper periphery of two calix[4]resorcinarenes. By treating activated esters 2a-b with excess corresponding amine such as 3-(dimethylamino)propylamine 3, -phenethylamine 4 and triethylenetetramine 5, six amide derivatives 6a~8b were obtained in high yield (Route 1). The pyridine-linked amide derivatives 9a-b were prepared by using acid chloride intermediate (Route 2). The amide derivatives 10a-b were obtained in moderate yields by direct alkylation of phenolic hydroxyl groups of 1a-b with N,N-dipropylchloroacetoamide in the presence of K2CO3/KI in acetone (Route 3).
Three different synthetic routes were developed to introduce carbamoyloxy functional groups at the upper periphery of two calix [4] resorcinarenes. By treating activated esters 2a-b with excess corresponding amine such as 3- (dimethylamino) propylamine 3, -phenethylamine 4 and triethylenetetramine 5 The pyridine-linked amide derivatives 9a-b were prepared by using acid chloride intermediate (Route 2). The amide derivatives 10a-b were obtained in high yield (Route 1) direct alkylation of phenolic hydroxyl groups of 1a-b with N, N-dipropylchloroacetoamide in the presence of K2CO3 / KI in acetone (Route 3).