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Molecules 2017, 22(5), 846; doi:10.3390/molecules22050846

Study on the Alkylation Reactions of N(7)-Unsubstituted 1,3-Diazaoxindoles

1
Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, 1475 Budapest, Hungary
2
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, P.O. Box 91, 1521 Budapest, Hungary
3
Department of Materials Technology, GAMF Faculty of Engineering and Computer Science, Pallasz Athéné University, P.O. Box 700, 6001 Kecskemét, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Richard A. Bunce
Received: 9 April 2017 / Revised: 13 May 2017 / Accepted: 16 May 2017 / Published: 19 May 2017
(This article belongs to the Collection Heterocyclic Compounds)

Abstract

The 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
Keywords: alkylation; lithiation; regioselectivity; 1,3-diazaoxindoles; by-products alkylation; lithiation; regioselectivity; 1,3-diazaoxindoles; by-products
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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