Evidence map›Paper›PMID 28035962›Full record

ReviewMolecules (Basel, Switzerland)2016

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.

Eszter Kókai, Gyula Simig, Balázs Volk

Abstract readReview
In one paragraph

Review in Molecules (Basel, Switzerland), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

  1. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

3 authors.

Eszter KókaiDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, P.O.B. 91, 1521 Budapest, Hungary. ekokai@mail.bme.hu.
Gyula SimigDirectorate of Drug Substance Development, Egis Pharmaceuticals PLC., P.O.B. 100, 1475 Budapest, Hungary. simig.gyula@egis.hu.
Balázs VolkDirectorate of Drug Substance Development, Egis Pharmaceuticals PLC., P.O.B. 100, 1475 Budapest, Hungary. volk.balazs@egis.hu.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

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.

Indexed as

ProtonsAlkylationCatalysisHalogensIndolesMolecular StructureOrganometallic CompoundsOxidation-ReductionOxindolesStereoisomerism2-oxindolebutyllithiumHalogensIndolesOrganometallic CompoundsOxindolesProtonsalkylationlithiationoxidationoxindoleregioselectivity

Identifiers

PMID28035962
PMCPMC6155829

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.