Evidence map›Paper›PMID 30156418›Full record

ArticleOrganic letters2018

Atypical Mode of [3 + 2]-Cycloaddition: Pseudo-1,3-dipole Behavior in Reactions of Electron-Deficient Thioamides with Benzynes.

Juntian Zhang, Annika C S Page, Vignesh Palani, Junhua Chen, Thomas R Hoye

Abstract read
In one paragraph

Article in Organic letters, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Review
  3. Article
  4. Review
  5. Direct observation ofChemical science · 2020
    Article
  6. 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

5 authors.

Juntian ZhangDepartment of Chemistry , University of Minnesota , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
Annika C S PageDepartment of Chemistry , University of Minnesota , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
Vignesh PalaniDepartment of Chemistry , University of Minnesota , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
Junhua ChenDepartment of Chemistry , University of Minnesota , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
Thomas R HoyeDepartment of Chemistry , University of Minnesota , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.ORCID 0000-0001-9318-1477

Funding

Synthesis, Structure, and Mechanism of Biorelevant Molecules and ReactionsR35GM127097 · NIGMS · UNIVERSITY OF MINNESOTA · PI THOMAS R. HOYE · 2018 to 2026
$3.5M
Synthesis Strategies for Bioactive Natural ProductsR01GM065597 · NIGMS · UNIVERSITY OF MINNESOTA TWIN CITIES · PI HOYE, THOMAS R. · 2002 to 2016
$3.1M
Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical ResearchS10OD011952 · OD · UNIVERSITY OF MINNESOTA · PI HOYE, THOMAS R. · 2012 to 2012
$378k
NIGMS NIH HHS R01 GM065597NIGMS NIH HHS R35 GM127097NIH HHS S10 OD011952
6 · The paper itself

Abstract

Thioamides bearing electron-withdrawing groups on the thiocarbonyl carbon atom react with benzynes [generated by the hexadehydro-Diels-Alder cycloisomerization] in an unprecedented fashion. Namely, the dihydrobenzothiazole products are consistent with a pathway involving initial formation of a stabilized ammonium ylide by a rare type of [3 + 2]-cycloaddition reaction. The fate of this species depends upon the nature of the R group(s) attached to the ylide nitrogen atom. The demonstration of new modes of reactivity represents the major advance arising from this study.

Indexed as

Ammonium CompoundsBenzene DerivativesBenzothiazolesCycloaddition ReactionElectronsMolecular StructureThioamidesAmmonium CompoundsBenzene DerivativesBenzothiazolesbenzyneThioamides

Identifiers

PMID30156418
PMCPMC6311210

What OpenQuestion holds

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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.