Synthesis and evaluation of new tri- and difluoromethyl containing 2,6,9-trioxabicyclo[3.3.1]nonanes

• Published in: Journal of fluorine chemistry Vol. 222-223; pp. 100 - 105
• Main Authors: Gerus, Igor I., Zhuk, Yury I., Tarasenko, Karen V., Shaitanova, Elena N., Sorochinskii, Alexandr E.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.06.2019; Elsevier; Elsevier BV
• Subjects: Chemical synthesis; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Crown ethers; Enones; Ethers; Intermediates; Macrocycles; Nonanes; Physical Sciences; Polyhaloalkyl ketones; Pyrimidinone; Science & Technology; Trihalogenomethyl-containing dicarbonyl compounds; Pyrimidinone; Macrocycles; Enones; Polyhaloalkyl ketones; Trihalogenomethyl-containing dicarbonyl compounds; ETHERS; ONE-STEP SYNTHESIS; ABSOLUTE-CONFIGURATION; FLUORINE; FACILE
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2019.04.017

[Display omitted] •The convenient synthesis of previously unknown fluoroalkyl containing. trioxabicyclo[3.3.1]nona-3,7-diene-4,8-dicarboxylate with four trifluoromethyl or two trifluoromethyl and two difluoromethyl groups in moderate yields was reported.•The synthesis is based on orthoacetate.•The chemical evaluation of synthesized bicycles was investigated.•New and perspective 2,6-bis(trifluoromethyl)pyrimidin-4(3 H)-one was synthesized. Enones 1, are examples of available and attractive building block which already has the polyfluoroalkyl group in blocks skeleton and their functionalization is an actual and perspective approach for the synthesis of more functionalized molecules. This approach led us to new polyfluoroalkyl containing trioxabicyclo[3.3.1]nona-3,7-diene-4,8-dicarboxylates with four trifluoromethyl or two trifluoromethyl and two difluoromethyl groups in moderate yields (up to 68%). These compounds are perspective as synthetic intermediates for preparation of new polyfluoromethyl containing heterocycles as well as their interaction into macrocycles system like crown ethers.