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 K 2 CO 3 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.