Synthesis of diaminomethylidene derivatives of tetronic acid |
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Authors: | M A Prezent V A Dorokhov |
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Institution: | 1221. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
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Abstract: | 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. |
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