Kokai E.,Budapest University of Technology and Economics |
Nagy J.,Budapest University of Technology and Economics |
Toth T.,Budapest University of Technology and Economics |
Kupai J.,Budapest University of Technology and Economics |
And 3 more authors.
Monatshefte fur Chemie | Year: 2016
Abstract: A new synthetic route was elaborated at our laboratory providing a convenient access to 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-ones (diazaoxindoles), a compound family of biological relevance. Treatment of the easily available ethyl 2-(4-chloropyrimidin-5-yl)acetate derivatives with ammonia afforded the corresponding 2-(4-aminopyrimidin-5-yl)acetamides, which were finally cyclized to the target compounds. Graphical abstract: [Figure not available: see fulltext.] © 2016 Springer-Verlag Wien
Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring
PubMed | Budapest University of Technology and Economics and Directorate of Drug Substance Development
Type: Journal Article | Journal: Molecules (Basel, Switzerland) | Year: 2016
The paper provides a comprehensive review of the base-catalysed C3-alkylation of N-unprotected-3-monosubstituted oxindoles. Based on a few, non-systematic studies described in the literature using butyllithium as the deprotonating agent, an optimized method has now been elaborated, via the corresponding lithium salt, for the selective C3-alkylation of this family of compounds. The optimal excess of butyllithium and alkylating agent, and the role of the halogen atom in the latter (alkyl bromides vs. iodides) were also studied. The alkylation protocol has also been extended to some derivatives substituted at the aromatic ring. Finally, various substituents were introduced into the aromatic ring of the N-unprotected 3,3-dialkyloxindoles obtained by this optimized method.