2-(<Emphasis Type="Italic">N</Emphasis>-Alkylamino)-1-(trifluoroacetimidoyl)vinyl ketone derivatives as potential reagents in heterocyclic synthesis

A reaction of 3-acetyl-4-amino-5,5,5-trifluoropent-3-en-2-one diphenylboron chelate and ammonia or primary amines affords 4-amino- or 4-alkylamino-3-trifluoroacetimidoylpent-3-en-2-ones, new reagents which can be used for the synthesis of pyrimidines with trifluoromethyl group.     

Synthesis of new pyrido[2,3-d]pyrimidine derivatives by three-component condensation of 5-acetyl-4-aminopyrimidines, cyclohexane-1,3-diones, and orthocarboxylic acid esters

A three-component condensation of 5-acetyl-4-aminopyrimidine derivatives with dimedone (or cyclohexane-1,3-dione) and triethyl orthoacetate (or triethyl orthopropionate) gave derivatives of 7-(1,3-dioxocyclohex-2-ylidene)-7,8-dihydropyrido[2,3-d]pyrimidine. These heterocyclic compounds containing the enamino ketone fragment can form boron chelates under the action of butoxy(diphenyl)borane. Dedicated to Academician O. M. Nefedov on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2006–2011, November, 2006.     

Pyrazol-5-one diaminomethylidene derivatives as reagents for the synthesis of heterocyclic compounds and as new chelating ligands

1-Arylpyrazol-5-ones added to the C≡N bond of benzoylcyanamide in the presence of Ni(OAc)₂, giving the corresponding pyrazol-5-one diaminomethylidene derivatives, which were used as reagents for the synthesis of heterocyclic compounds and as chelating ligands.     

Reactions of alkyl acetone-1,3-dicarboxylates with cyanamide and benzoylcyanamide

The reactions of cyanamide with dialkyl acetone-1,3-dicarboxylates in the presence of nickel acetylacetonate afforded alkyl 2-amino-4-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylates. The same compounds were obtained by intramolecular cyclization of adducts of acetone-1,3-dicarboxylates with benzoylcyanamide under the action of sodium alkoxides. Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1304–1306, May, 2005.     

Addition of barbituric acids to benzoylcyanamide

Derivatives of 5-diaminomethylenepyrimidine-2,4,6-trione were synthesized by adding barbituric andN,N′-dicyclohexylbarbituric acids to benzoylcyanamide in the presence of stoichiometric amounts of Ni(OAc)₂. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1701–1703, September, 1997.