Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VIII. Synthesis and Properties of N-[(3-Chloroadamantan-1-yl)methyl]-N′-(Fluoro, chlorophenyl)ureas and Symmetrical Bis-ureas

Abstract

A new procedure has been proposed for the synthesis of 3-chloroadamantan-1-ylmethyl isocyanate starting from 2-(3-chloroadamantan-1-yl)acetic acid. Reactions of 3-chloroadamantan-1-ylmethyl isocyanate with fluoro- and chloroanilines and alkane-α,ω-diamines afforded two series of N,N′-disubstituted ureas containing a 3-chloroadamantan-1-yl substituent in 53–94% yields. The synthesized ureas are promising as inhibitors of human soluble epoxide hydrolase.