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Record W4384499677 · doi:10.1021/acsomega.3c00961

Synthesis of 3-Alkyl Oxazolidines, Derived from 2-Hydroxymethyl Piperidine, as Analytical Standards for the Analysis of Volatile Aldehydes in the Workplace

2023· article· en· W4384499677 on OpenAlex
Amadou R. Yaya, Martin Girard, Karima Belkhadem, Rémi Piard, A. Decken, Catherine Choinière, Pierre Luc Cloutier, Jacques Lesage, Livain Breau

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueACS Omega · 2023
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Reactivity of Sulfur-Containing Compounds
Canadian institutionsInstitut de recherche Robert-Sauvé en santé et en sécurité du travailUniversity of New BrunswickUniversité du Québec à Montréal
FundersInstitut de Recherche Robert-Sauvé en Santé et en Sécurité du TravailUniversité du Québec à Montréal
KeywordsChemistryAcroleinIminiumAlkylPiperidineHydroxymethylDiastereomerPyridineEnamineHemiaminalOrganic chemistryAldehydeMedicinal chemistryIonCatalysis

Abstract

fetched live from OpenAlex

High Resolution Image Download MS PowerPoint Slide Hexahydro-3-alkyl-3 H -oxazolo[3,4- a ]pyridines 4–15 for the quantitative analysis of various aldehydes were obtained in good yield via the condensation reaction of 2-hydroxymethylpiperidine (2-HMP) with aldehydes under mild conditions. When acrolein was used, the bicyclic 17 was obtained. This novel compound has suitable physical characteristics for an analytical standard. The hexahydro-3-vinyl-3 H -oxazolo[3,4- a ]pyridine 16 can be obtained at higher temperatures using an excess of acrolein (3 equiv). Following the same procedure as for 16, but with an excess of 2-HMP (2 equiv), a diastereomeric mixture of 18 / 19, which are both bisadducts of 2-HMP with acrolein, was obtained. The latter mixture can be easily converted into pure 18 . Mechanistically, a thorough 1 H-NMR study did not show any evidence that the condensation reaction proceeded via an enamine. The reaction probably proceeded through an elusive hemiaminal and fleeting iminium ion, which underwent subsequent cyclization to give hexahydro-3-alkyl-3 H -oxazolo[3,4- a ]pyridines 4 – 16 . The reaction pathways for the preparation of 4–18 are described.

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.

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)0.001
metaresearch head score (Gemma)0.002
Version: codex-gemma-dda1882f352aValidation 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 score0.063
Threshold uncertainty score0.575

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.002
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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 head0.025
GPT teacher head0.294
Teacher spread0.270 · 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