Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

Tamie Suzuki, Nilamber A Mate, Arijit A Adhikari, John D Chisholm

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2019. 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.

Formation of PyrroloindolinesTetrahedron letters · 2021
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

4 authors.

Tamie SuzukiDepartment of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.ORCID 0000-0003-3753-5204

Nilamber A MateDepartment of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.ORCID 0000-0002-4441-7188

Arijit A AdhikariDepartment of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.

John D ChisholmDepartment of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, NY 13244-4100, USA.ORCID 0000-0001-9518-2393

Funding

New Methods for the Synthesis of PyrroloindolinesR15GM116054 · NIGMS · SYRACUSE UNIVERSITY · PI CHISHOLM, JOHN DANIEL · 2015 to 2015

$318k

American Chemical Society Petroleum Research Fund 54823-ND1NIGMS NIH HHS R15 GM116054NIGMS NIH HHS R15-GM116054

6 · The paper itself

Abstract

2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

Indexed as

AcetamidesCatalysisChloroacetatesIndolesLewis AcidsStereoisomerismAcetamidesChloroacetatesIndolesLewis Acidstrichloroacetamidedialkylationindoleindoleninespiroindolinetrichloroacetimidate

Identifiers

PMID31731742

DOI10.3390/molecules24224143

PMCPMC6891773

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LicenceCC BY

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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.