Evidence map›Paper›PMID 34080279›Full record

ArticleAngewandte Chemie (International ed. in English)2021

Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.

Melissa Ramirez, Evan R Darzi, Joyann S Donaldson, Kendall N Houk, Neil K Garg

Abstract read

In one paragraph

Article in Angewandte Chemie (International ed. in English), 2021. 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.

Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.Organic letters · 2024
Article
Aryne-Enabled C-N Arylation of Anilines.Angewandte Chemie (International ed. in English) · 2023
Article
Facile synthesis of 2-aza-9,10-diphenylanthracene and the effect of precise nitrogen atom incorporation on OLED emitters performance.Materials advances · 2023
Article
Nonlinear Optical Properties of Pyrene Derivatives Based on a Donor-Acceptor Structure and Its Polyurethane Composites.ACS omega · 2022
Article
A sequential cyclization/π-extension strategy for modular construction of nanographenes enabled by stannole cycloadditions.Chemical science · 2022
Article
Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.JACS Au · 2021
Review

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.

Melissa RamirezDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.

Evan R DarziDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.

Joyann S DonaldsonDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.

Kendall N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.

Neil K GargDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.ORCID http://orcid.org/0000-0002-7793-2629

Funding

Exploiting Unconventional Building Blocks in Chemical SynthesisR35GM139593 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI Neil K. Garg · 2021 to 2026

$4.0M

Harnessing Strained Intermediates to Access Complex MoleculesR01GM132432 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI GARG, NEIL K · 2019 to 2020

$735k

Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical ResearchS10RR025631 · NCRR · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2009 to 2009

$328k

Methodology towards the synthesis of complex stereochemically dense natural productsF32GM122245 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI DARZI, EVAN RASHIED · 2017 to 2019

$160k

Cycloadditions of Strained Cyclic IntermediatesF31GM130099 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI RAMIREZ, MELISSA · 2019 to 2021

$90k

Directorate for Computer and Information Science and Engineering OCI-1053575Division of Chemistry CHE-1048804Division of Chemistry CHE-1764328NCRR NIH HHS S10 RR025631NCRR NIH HHS S10RR025631NIGMS NIH HHS F31 GM130099NIGMS NIH HHS F31 GM130099-02NIGMS NIH HHS F32 GM122245NIGMS NIH HHS F32-GM122245NIGMS NIH HHS R01 GM132432NIGMS NIH HHS R35 GM139593

6 · The paper itself

Abstract

We report a computational and experimental study of the reaction of oxadiazinones and strained alkynes to give polycyclic aromatic hydrocarbons (PAHs). The reaction proceeds by way of a pericyclic reaction cascade and leads to the formation of four new carbon-carbon bonds. Using M06-2X DFT calculations, we interrogate several mechanistic aspects of the reaction, such as why the use of non-aromatic strained alkynes can be used to access unsymmetrical PAHs, whereas the use of arynes in the methodology leads to symmetrical PAHs. In addition, experimental studies enable the rapid synthesis of new PAHs, including tetracene and pentacene scaffolds. These studies not only provide fundamental insight regarding the aforementioned cycloaddition cascades and synthetic access to PAH scaffolds, but are also expected to enable the synthesis of new materials.

Indexed as

arynescyclic alkynescycloadditionsdensity functional theorypolycyclic aromatic hydrocarbons

Identifiers

PMID34080279

DOI10.1002/anie.202105244

PMCPMC8338799

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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.