Study on the Alkylation Reactions of N(7)-Unsubstituted 1,3-Diazaoxindoles
AbstractThe chemistry of the 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (1,3-diazaoxindole) compound family, possessing a drug-like scaffold, is unexplored. In this study, the alkylation reactions of N(7)-unsubstituted 5-isopropyl-1,3-diazaoxindoles bearing various substituents at the C(2) position have been investigated. The starting compounds were synthesized from the C(5)-unsubstituted parent compounds by condensation with acetone and subsequent catalytic reduction of the 5-isopropylidene moiety. Alkylation of the thus obtained 5-isopropyl derivatives with methyl iodide or benzyl bromide in the presence of a large excess of sodium hydroxide led to 5,7-disubstituted derivatives. Use of butyllithium as the base rendered alkylation in the C(5) position possible with reasonable selectivity, without affecting the N(7) atom. During the study on the alkylation reactions, some interesting by-products were also isolated and characterized. View Full-Text
- Supplementary File 1:
ZIP-Document (ZIP, 1179 KB)
Share & Cite This Article
Kókai, E.; Halász, J.; Dancsó, A.; Nagy, J.; Simig, G.; Volk, B. Study on the Alkylation Reactions of N(7)-Unsubstituted 1,3-Diazaoxindoles. Molecules 2017, 22, 846.
Kókai E, Halász J, Dancsó A, Nagy J, Simig G, Volk B. Study on the Alkylation Reactions of N(7)-Unsubstituted 1,3-Diazaoxindoles. Molecules. 2017; 22(5):846.Chicago/Turabian Style
Kókai, Eszter; Halász, Judit; Dancsó, András; Nagy, József; Simig, Gyula; Volk, Balázs. 2017. "Study on the Alkylation Reactions of N(7)-Unsubstituted 1,3-Diazaoxindoles." Molecules 22, no. 5: 846.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.