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Record W4404893506 · doi:10.1016/j.tetlet.2024.155396

O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species

2024· article· en· W4404893506 on OpenAlexafffund
Guillaume Reynard, Calvine Lai, Emna Azek, H. Lebel

Bibliographic record

VenueTetrahedron Letters · 2024
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsCentre in Green Chemistry and Catalysis
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of WaterlooAlliance de recherche numérique du CanadaFonds de recherche du Québec – Nature et technologiesUniversité de MontréalSimon Fraser UniversityCanada Foundation for Innovation
KeywordsChemistryAlkylationAlkylTransient (computer programming)Organic chemistryCatalysis

Abstract

fetched live from OpenAlex

Diazotisation of amines with a nitrite reagent was performed in the presence of hydroxy-pyridines and derivatives to give the alkylation products. The O -alkylation product was isolated from 2-, 3-, 4-hydroxypyridines, 2-hydroxyquinoline and 2-hydroxypyrimidines. In the case of 2-hydropyridines, the N -alkylation product was also observed, with the O -alkylation product being favoured. The reaction conditions were compatible with a variety of functional groups, and namely amino alcohols were successfully reacted to afford hydroxy-substituted products. The distinctive reactivity of dinitrites in comparison to mononitrites is also addressed.

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 distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
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 score0.095
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

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

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 head0.017
GPT teacher head0.255
Teacher spread0.238 · 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 teacher head, not a consensus.

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

Citations1
Published2024
Admission routes2
Has abstractyes

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