Evidence map›Paper›PMID 29164878›Full record

ArticleThe Journal of organic chemistry2017

Thermal Hetero-Diels-Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones.

Thomas Wurm, Ben W H Turnbull, Brett R Ambler, Michael J Krische

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Article
  3. 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.

Thomas WurmDepartment of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
Ben W H TurnbullDepartment of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
Brett R AmblerDepartment of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
Michael J KrischeDepartment of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.ORCID 0000-0001-8418-9709

Funding

Substituted Piperidine Formation via C-C Bond Forming Transfer HydrogenationR01GM069445 · NIGMS · UNIVERSITY OF TEXAS AUSTIN · PI KRISCHE, MICHAEL J · 2005 to 2024
$6.7M
NIGMS NIH HHS R01 GM069445
6 · The paper itself

Abstract

Benzocyclobutenones 1a-1g undergo cycloreversion at 150 °C in m-xylene solvent to form transient α-oxo-ortho-quinodimethanes or "ortho-quinoid ketene methides", which engage in intermolecular [4+2] cycloadditions with isatins 2a-2f to form 2-oxindole spirolactones 3a-3l. This process tolerates an array of different functional groups and substitution patterns, and is applicable to unprotected isatins 2b-2f bearing free NH-functionalities. The superior performance of isatins compared to other carbonyl based dienophiles was demonstrated and rationalized with the aid of quantum chemical calculations.

Indexed as

Quantum TheoryCycloaddition ReactionIsatinOxindolesPolycyclic CompoundsSpironolactoneTemperature2-oxindolebenzocyclobuteneIsatinOxindolesPolycyclic CompoundsSpironolactone

Identifiers

PMID29164878
PMCPMC5757836

What OpenQuestion holds

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Registered trials

None linked

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.