M. A. Prezent

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.

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

Abstract1-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.

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.

Camps reaction for the synthesis of 3-RS-4-arylquinolin-2-ones

The replacement of the chlorine atom in 2-(chloroacetamido)benzophenones on treatment with RSH (R = Alk, Ar, Hetaryl) in the presence of MeONa is accompanied by intramolecular cyclization following the Camps reaction pattern to give 3-RS-4-arylquinolin-2-ones. Cleavage of 4-aryl-3-(benzoxazol-2-ylthio)quinolin-2-ones by morpholine has resulted in the corresponding 4-aryl-3-mercaptoquinolin-2-ones.

Synthesis of diaminomethylidene derivatives of tetronic acid

Methyl 4-chloro-3-oxobutanoate reacts with benzoylcyanamide in the presence of catalytic amounts of Ni(acac)2 to give the corresponding ketene N-benzoylaminal, which is transformed in boiling AcOH into 3-[(amino)(benzoylamino)methylidene]tetrahydrofuran-2,4-dione. Debenzoylation of the latter in the presence of EtONa in EtOH yields a N,N-unsubstituted diaminomethylidene derivative of tetronic acid. Cyclization of the adduct of methyl 4-chloro-3-oxobutanoate with benzoylcyanamide in the presence of triethylamine follows a different pathway leading to methyl 2-amino-1-benzoyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate.

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.