Synthesis of lateral macrobicyclic cryptand

This paper deals with the synthesis of a new lateral macrobicyclic cryptand 10. Condensation of 2.6-di(bromomethyl)pyridine with 3-(n-tosylamino) methyl propionate in the presence of anhydrous K₂CO₃ at room temperature gave 5 which was hydrolyzed to 6. Reaction of the latter with excess sulfonyl chloride afforded 2,6-di(4′-chloroformyl-2′-tosyl-2′-azabutyl)pyridine (7). Pentaaza-1,5,13,17,28-dithia-20,25-tricyclo [15,5,5,1^7,11]-octacosa-7,9,11 (28)-triene(10) has been synthesized by the following sequence of reactions: Condensation of 7 with 1,7-diaza-4,10-dithia-dodecane (3) by high dilution technique in toluene-THF at room temperature afforded 8 which was reduced by diborane in THF solution to give 9. Treatment of 9 with sodium anthracene in monoglyme produced 10.