Convenient Method for the Synthesis of Macrocyclic Teteraamides, Acyclic Diamides, their Lariat Derivatives and Bis-macrocyclic Tetraamides

 

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Abstract

The macrocyclic tetraamides 8a-e were obtained in good yields by bis-alkylation of the potassium salts of the appropriate bis-phenols 7a-c with the dihalo compounds 2a,b. Similarly, macrocyclic tetraamides with pendant hydroxy group 18a,b were prepared by the nucleophilic reaction of the potassium salts of 7a,b with the dihalo compound 10. Acylation of 18a,b with chloroacetyl chloride gave the corresponding ester 19a,b. Compounds 19a,b reacted with different secondary amines to afford the corresponding lariat macrocycles 20a-d and novel bis-macrocycle 21 in 50-65% yield.

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