2-Acylcycloalkanones having polyfluoroalkyl groups react with guanidine, urea, thiourea, methylisothiourea, benzamidine, guanylthiourea, dicyanodiamide, and trifluoroacetylurea by Lewisacid catalysis to form the corresponding 5,6-oligomethylene pyrimidines. A decrease in the yields along with increase of polyflyoroalkyl 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.

Efficient procedures for the regioselective synthesis of fluoroalkyl-containing three-, five-, six-, and seven-membered heterocycles as well as of related fused compounds, namely, ct,13-epoxyketones, ct,13-aziridinylketones, pyrazoles, pyrazolines, isoxazolines, 1,2-dithiolenes, amino-and mercaptopyrimidines, A3.~-2-thioxo-l,3,2-thiazaphosphorines, A~.5-2-thioxo -1,3,2-oxazaphosphorines, 2,3-dihydro-1,4-diazepines, azidno[ 1,2-a]quinoxalines, benzo[b]-and naphtho[2,3-bl-l,4-diazepines, and triazolopyridazines, which have been developed by the authors and coworkers, are summarized. The a-and It-functionalized fluoroalkylcontaining carbonyl compounds (13-diketones, 13-ketoesters, their salts, regioisomeric ~3-aminovinyl ketones, 13-aminovinylthiones, [3-hydroxyketones, a,[3-enones, and their halogen der-vatives) were used as synthons in the processes of formation of the above-mentioned heterocycles.

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