We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments. XX. N-[(3,5-Difluoroadamantan-1-yl)]-N′-R-ureas and Symmetrical Bis-ureas.
- Authors
Gladkikh, B. P.; Danilov, D. V.; D'yachenko, V. S.; Burmistrov, V. V.; Butov, G. M.; Novakov, I. A.
- Abstract
A procedure has been developed for the synthesis of 3,5-difluoroadamantan-1-yl isocyanate from 3,5-difluoroadamantane-1 carboxylic acid and diphenylphosphoryl azide using a new fluorinating agent, Ishikawa reagent, in one stage of the synthesis. The reaction of 3,5-difluoroadamantan-1-yl isocyanate with aliphatic diamines and trans-4-[(4-aminocyclohexyl)oxy]benzoic acid afforded a series of N,N′-disubstituted ureas and bis-ureas in 43–96% yields. The hydrolysis of 3,5-difluoroadamantan-1-yl isocyanate in the presence of a catalytic amount of DBU gave symmetrical N,N′-bis(3,5-difluoroadamantan-1-yl)urea in 47% yield. A relation between the number of fluorine atoms in the adamantane fragment on the melting points and lipophilicities of the synthesized ureas has been revealed, which makes it possible to control these important properties of ureas as potential enzyme inhibitors.
- Subjects
EPOXIDE hydrolase; ADAMANTANE derivatives; MELTING points; BENZOIC acid; CARBOXYLIC acids; ISOCYANATES
- Publication
Russian Journal of Organic Chemistry, 2024, Vol 60, Issue 6, p1066
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428024060125