Evidence map›Paper›PMID 40786882›Full record

ArticleACS organic & inorganic Au2025

Solvents' and Reagents' Noninnocent Roles in the Groebke-Blackburn-Bienaymé (GBB) Multicomponent Reaction: Experimental and Computational Evidence.

Marcelo H R Carvalho, Pedro P De Castro, Pedro Beck, Hélio F Dos Santos, Fabricio Machado, José R Correa, Brenno A D Neto, Giovanni W Amarante

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in ACS organic & inorganic Au, 2025. 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. Article
  2. 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

8 authors.

Marcelo H R CarvalhoChemistry Department, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, Minas Gerais 36036-900, Brazil.
Pedro P De CastroPharmacy Department, Federal University of Juiz de Fora, Campus Governador Valadares, Governador Valadares, Minas Gerais 35010-180, Brazil.ORCID https://orcid.org/0000-0002-3018-3130
Pedro BeckLaboratory of Medicinal and Technological Chemistry, Chemistry Institute (IQ-UnB), University of Brasília, Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70910-900, Brazil.
Hélio F Dos SantosChemistry Department, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, Minas Gerais 36036-900, Brazil.
Fabricio MachadoLaboratory of Medicinal and Technological Chemistry, Chemistry Institute (IQ-UnB), University of Brasília, Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70910-900, Brazil.ORCID https://orcid.org/0000-0002-3041-1906
José R CorreaLaboratory of Medicinal and Technological Chemistry, Chemistry Institute (IQ-UnB), University of Brasília, Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70910-900, Brazil.
Brenno A D NetoLaboratory of Medicinal and Technological Chemistry, Chemistry Institute (IQ-UnB), University of Brasília, Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal 70910-900, Brazil.ORCID https://orcid.org/0000-0003-3783-9283
Giovanni W AmaranteChemistry Department, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, Minas Gerais 36036-900, Brazil.ORCID https://orcid.org/0000-0003-1004-5395

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Despite the frequent use of alcohols as solvents in GBB (Groebke-Blackburn-Bienaymé) protocols, the mechanistic reasons for their preference remain poorly understood. In this work, we combined experimental and theoretical investigations to elucidate the roles of solvents and reagents in the GBB reaction, revealing their noninnocent behavior. Kinetic experiments, high-resolution ESI-(+)-MS-(/MS), and DFT calculations demonstrated that methanol not only acts as a solvent but also as a cocatalyst, significantly influencing the reaction mechanism and accelerating key steps. We proposed both uncatalyzed and PTSA-catalyzed pathways, including alternative mechanisms involving solvent-participating intermediates. The reaction scope confirmed the method's robustness, and selected fluorescent products were successfully applied as bioimaging probes in live cells. These findings contribute to a deeper understanding of MCR mechanisms and highlight the critical impact of solvent and reagent effects on their efficiency.

Indexed as

bioimaging experimentscatalysisDFTimidazo[1,2-a]heterocyclesmechanismmulticomponent reactionsolvent effect

Identifiers

PMID40786882
PMCPMC12332792

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.