An improved and versatile synthetic route to 6,7:13,14-dibenzo-1,8,4,11-dioxadiazacyclotetradecane

A new and effective synthetic pathway to 6,7:13,14-dibenzo-1,8,4,11-dioxadiazacyclotetradecane (1) has been developed. Beginning from salicylic acid, this synthetic pathway involves five high yielding steps to afford the macrocycle 6,7:13,14-dibenzo1,8,4,1 1-dioxadiazacylotetradecane-3,10-dione. Reduction of this macrocycle afforded the dioxadiaza crown 1 with an overall yield of 60%. (C) 2003 Elsevier B.V. All rights reserved.