Evidence map›Paper›PMID 40608800›Full record

ArticleChemPlusChem2025

A Base-Mediated Rearrangement of the Benzylic 1,5-Hexadipyridynyl Moiety.

Wouter A Remmerswaal, Thai-Tony Nguyen, Zijian Han, Fedor Krasovski Slobodian, Ruisheng Xiong, Vadim Kessler, Zhijian Xu, Weiliang Zhu, Mate Erdelyi

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in ChemPlusChem, 2025. 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

9 authors.

Wouter A RemmerswaalDepartment of Chemistry - BMC, Uppsala University, 751 23, Uppsala, Sweden.ORCID https://orcid.org/0000-0002-1040-4311
Thai-Tony NguyenDepartment of Chemistry - BMC, Uppsala University, 751 23, Uppsala, Sweden.ORCID https://orcid.org/0009-0001-6232-8322
Zijian HanState Key Laboratory of Drug Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.ORCID https://orcid.org/0009-0000-0839-6386
Fedor Krasovski SlobodianDepartment of Chemistry - BMC, Uppsala University, 751 23, Uppsala, Sweden.ORCID https://orcid.org/0009-0007-7775-3691
Ruisheng XiongDepartment of Chemistry - BMC, Uppsala University, 751 23, Uppsala, Sweden.ORCID https://orcid.org/0000-0002-8165-5863
Vadim KesslerDepartment of Molecular Sciences, BioCenter Swedish University of Agricultural Sciences, 750 07, Uppsala, Sweden.ORCID https://orcid.org/0000-0001-7570-2814
Zhijian XuState Key Laboratory of Drug Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.ORCID https://orcid.org/0000-0002-3063-8473
Weiliang ZhuState Key Laboratory of Drug Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.ORCID https://orcid.org/0000-0001-6699-5299
Mate ErdelyiDepartment of Chemistry - BMC, Uppsala University, 751 23, Uppsala, Sweden.ORCID https://orcid.org/0000-0003-0359-5970

Funding

Carl Trygger Foundation 23:2764Department of Chemistry-BMC and the Disciplinary Domain of Medicine and PharmacyDutch Research Council 019.242EN.022National Academic Infrastructure for Supercomputing in Sweden 2025/5-155National Academic Infrastructure for Supercomputing in Sweden NAISSNSFC-STINT joint 82211530060Swedish Research Council 2024-05496
6 · The paper itself

Abstract

A previously unrecognized base-mediated rearrangement of a benzylic 1,5-hexadipyridynyl moiety is reported. Upon exposure to base, this structural motif rearranges into a constrained vinyl-pyridine substituted cyclobutene. Computational modeling indicates that the rearrangement takes place following a route involving stepwise deprotonation, shifted reprotonation, and 4π-electrocyclization. The reaction rate and the stereochemical outcome is consistent with the experimental observations. Furthermore, nonbase mediates rearrangements, through well-known Cope-like [3,3]-sigmatropic shifts, are found to be high in energy, and therefore, take a backseat to the base-mediated pathway. This rearrangement may provide a novel reactivity pathway of conjugated systems for synthetic methodology development.

Indexed as

density functional theorymechanismreactivityrearrangement

Identifiers

PMID40608800
PMCPMC12435124

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.