PREPARATION OF A VARIETY OF MACROCYCLIC DIAMIDES AND TETRAAMIDES AND THEIR PERAZA-CROWN ANALOGS USING THE CRAB-LIKE CYCLIZATION REACTION

Twelve new macrocyclic di‐ and tetraamides have been synthesized from the reaction of a bis(α‐chloroamide) with a primary amine or with a diamine. Some of these cyclic di‐ and tetraamides contained pendant aminoalkyl groups attached on one or more ring nitrogen atoms. Two macrocyclic dithiadiamides were prepared from the reaction of a bis(α‐chloroamide) and a dimercaptan. In every case, 12‐, 14‐ and 15‐membered cyclic di‐ and tetraamides were isolated in good yields. The 9‐, 17‐ and 18‐membered macrocycles were prepared in lower yields. Four of the amide‐containing macrocycles were reduced by diborane to the perazacrown compounds. Copyright © 1990 Journal of Heterocyclic Chemistry