Evidence map›Paper›PMID 35811875›Full record

ArticleACS omega2022

Mechanism of the Aza-Piancatelli Reaction: Scope and Limitations of Furan Substitution in Donor-Acceptor Stenhouse Adduct Synthesis.

Beatriz Peñín, Nil Sanosa, Diego Sampedro, Ignacio Funes-Ardoiz

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In one paragraph

Article in ACS omega, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Review
  2. 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

4 authors.

Beatriz PeñínDepartamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain.
Nil SanosaDepartamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain.
Diego SampedroDepartamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain.ORCID https://orcid.org/0000-0003-2772-6453
Ignacio Funes-ArdoizDepartamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain.ORCID https://orcid.org/0000-0002-5843-9660

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The aza-Piancatelli reaction has been widely used to synthesize donor-acceptor Stenhouse adducts (DASAs), a new class of molecular photoswitches with unique properties. However, the substitution pattern of furan cores has been limited to position 3, as 3,4-disubstituted furans remain unreactive. Herein, we explore the aza-Piancatelli reaction mechanism using density functional theory (DFT) calculations to understand the influence of the different substituents on the reactivity. We found that all the reaction pathways are kinetically accessible, but the driving force of the reaction is lost in disubstituted furans due to the loss of conjugation in the DASA products. Finally, a simple model is proposed to guide the design of synthetic routes using this reaction.

Identifiers

PMID35811875
PMCPMC9261078

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.