Next Article in Journal
Rate of Homologous Desensitization and Internalization of the GLP-1 Receptor
Previous Article in Journal
A Multifunctional and Possible Skin UV Protectant, (3R)-5-Hydroxymellein, Produced by an Endolichenic Fungus Isolated from Parmotrema austrosinense
Article Menu
Issue 1 (January) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(1), 24; doi:10.3390/molecules22010024

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

1
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, P.O.B. 91, 1521 Budapest, Hungary
2
Directorate of Drug Substance Development, Egis Pharmaceuticals PLC., P.O.B. 100, 1475 Budapest, Hungary
3
Department of Materials Technology, GAMF Faculty of Engineering and Computer Science, Pallasz Athéné University, P.O.B. 700, 6001 Kecskemét, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 5 November 2016 / Revised: 15 December 2016 / Accepted: 17 December 2016 / Published: 26 December 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [2674 KB, uploaded 27 December 2016]   |  

Abstract

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. View Full-Text
Keywords: oxindole; alkylation; lithiation; regioselectivity; oxidation oxindole; alkylation; lithiation; regioselectivity; oxidation
Figures

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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Kókai, E.; Simig, G.; Volk, B. 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. Molecules 2017, 22, 24.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top