Synthesis of novel amide-crownophanes and Schiff base-crownophanes based on p-phenylene, 2,6-naphthalene, and 9,10-anthracene

Article abstract of DOI:10.1002/jhet.129

(Chemical Equation Presented) The novel macrocyclic diamides 11-13, 16-18 are obtained in 45-66% yields by the reaction of dipotassium salts 10a-c and 15 with each of 1,4-di(bromomethyl)benzene 4, 2,6-di(bromomethyl)naphthalene 6 and 9,10-di(bromomethyl)anthracene 8, repectively, in boiling DMF. On the other hand, the new macrocyclic Schiff bases 28 and 29 are obtained in 44% and 42% yields by heating the appropriate bis-amines 25b, 26b with the corresponding bis-aldehydes 21, 22, respectively, in refluxing acetic acid under high-dilution conditions.