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Record W7116781330 · doi:10.1021/acs.joc.5c02194

Regioselective Introduction of Indolin-3-one Moieties to Substituted Heteroaromatic Compounds

2025· article· en· W7116781330 on OpenAlexafffund
Andrew J. Daszczynski, Nina Bui, F. G. West

Bibliographic record

VenueThe Journal of Organic Chemistry · 2025
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Characterization of Pyrroles
Canadian institutionsUniversity of Alberta
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of Alberta
KeywordsRegioselectivityElectrophileNucleophileCatalysisSelectivityMoietySurface modification

Abstract

fetched live from OpenAlex

C2-substituted indolin-3-ones are formed via a mild dual catalytic method involving the generation of a reactive C -acylimine species that can be intercepted by a variety of nucleophilic arenes. The transient C -acylimine electrophile could be trapped regioselectively by a variety of arenes, on which the most reactive site was blocked, offering a new scope of products. Competition experiments show that the C -acylimine electrophile exhibits selectivity for pyrrole over other heteroaromatic traps. Indolin-3-one functionalization of melatonin, protected amino acids, and dipeptides showcases the potential of this chemistry for late-stage diversification of biomolecules containing electron-rich arene units.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.004

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0010.001

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.008
GPT teacher head0.215
Teacher spread0.207 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations0
Published2025
Admission routes2
Has abstractyes

Explore more

Same venueThe Journal of Organic ChemistrySame topicSynthesis and Characterization of PyrrolesFrench-language works237,207