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Synthesis 2000; 2000(12): 1738-1748
DOI: 10.1055/s-2000-8200
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Syntheses of Novel 4-Polfluoroalkyl-Substituted 5,6-Oligomethylene Pyrimidines

Dmitrii V. Sevenard* , Oleg G. Khomutov, Olga V. Koryakova, Valeriya V. Sattarova, Mikhail I. Kodess, Johannes Stelten, Ildiko Loop, Enno Lork, Kazimir I. Pashkevich, Gerd-Volker Röschenthaler
  • *Institute of Inorganic and Physical Chemistry, University of Bremen, Leobener Strasse, D-28334 Bremen, Germany; Fax +49 (4 21) 2 18 42 67; E-mail: gvr@chemie.uni-bremen.de
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Publication Date:
31 December 2000 (online)

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2-Acylcycloalkanones having polyfluoroalkyl groups react with guanidine, urea, thiourea, methylisothiourea, benzamidine, guanylthiourea, dicyanodiamide, and trifluoroacetylurea by Lewis-acid catalysis to form the corresponding 5,6-oligomethylene pyrimidines. A decrease in the yields along with increase of polyfluoroalkyl substituent length in the molecule of the starting 1,3-diketone was observed in the case of reagents with lower nucleophilicity (urea, thiourea, dicyanodiamide). The pyrimidines obtained from aromatic aldehydes showed E-configuration with respect to the arylidene double bond. Tautomeric structures as a function of the substituent in 2 position in the pyrimidine ring both in liquid and solid state were investigated by X-ray diffraction, IR and NMR spectroscopy.

2-polyfluoroacyl cycloalkanones - urea - guanidines - benzamidine - pyrimidines - tautomerism - Lewis acids - cyclizations - heterocycles