Synthesis and properties of 1-[(3-fluoroadamantan-1-yl)methyl]-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis{3-[(3-fluoroadamantan-1-yl)methyl]ureas} as promising soluble epoxide hydrolase inhibitors

A two-step procedure to synthesize (3-fluoroadamantan-1-yl)methyl isocyanate from (3-hydroxyadamantane)acetic acid that involves fluorination with Ishikawa’s reagent on the first step of the synthesis was developed. The reaction of (3-fluoroadamantan-1-yl)methyl isocyanate with aliphatic diamines ga...

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Bibliographic Details
Published in:Russian chemical bulletin 2022, Vol.71 (1), p.107-113
Main Authors: Danilov, D. V., D’yachenko, V. S., Burmistrov, V. V., Butov, G. M., Novakov, I. A.
Format: Article
Language:English
Subjects:
Acetic acid
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Diamines
Fluorination
Fluorine
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Industrial accidents
Inorganic Chemistry
Melting points
Methyl isocyanate
Organic Chemistry
Reagents
Ureas
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Summary:A two-step procedure to synthesize (3-fluoroadamantan-1-yl)methyl isocyanate from (3-hydroxyadamantane)acetic acid that involves fluorination with Ishikawa’s reagent on the first step of the synthesis was developed. The reaction of (3-fluoroadamantan-1-yl)methyl isocyanate with aliphatic diamines gave 1,3-disubstituted bis-diureas in 60–97% yields. A strong decrease in the melting points of the obtained ureas (up to ∼70–144 °C) was observed upon introduction of the fluorine atoms at the bridgehead positions of the adamantane unit.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-022-3383-8