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Record W3043808583 · doi:10.1139/cjc-2020-0145

Facile and green synthesis of a series of dihydro-[1,2,4]triazolo[1,5-<i>a</i>]pyrimidine scaffolds

2020· article· en· W3043808583 on OpenAlex

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.

venuePublished in a venue whose home country is Canada.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueCanadian Journal of Chemistry · 2020
Typearticle
Languageen
FieldChemistry
TopicMulticomponent Synthesis of Heterocycles
Canadian institutionsnot available
Fundersnot available
KeywordsChemistryPiperidineCatalysisMoietyOrganic chemistryGreen chemistrySolventCombinatorial chemistryPyrimidineSubstrate (aquarium)Ionic liquidStereochemistry

Abstract

fetched live from OpenAlex

This work presents a new catalytic application of 4,4′-trimethylenedipiperidine for the efficient synthesis of a series of dihydro-[1,2,4] triazolo[1,5-a]pyrimidines. According to the principles of green chemistry, the reaction was performed (a) in a solvent mixture comprised of water and ethanol (1:1 v/v) at reflux temperature and (b) solvent-free grinding in a mortar by a pestle. The organocatalyst could be reused up to 10 runs, and no reduction of catalytic activity was detected. A variety of substituted dihydro-[1,2,4] triazolo[1,5-a]pyrimidines were obtained in good to excellent yields under eco-friendly conditions. 4,4′-Trimethylenedipiperidine is commercially available and easy to handle, and it also shows high thermal stability and good solubility in water. This work revealed that this organocatalyst, a hydrogen bond donor to active carbonyl groups and simultaneously a Lewis base through the nitrogen atom of second piperidine moiety, could play a vital role in the promotion of the one-pot multi-component reactions. The main merits of the current methodology include short reaction time, wide substrate scope, use of a metal-free catalyst and green solvents, and simple work-up process. Furthermore, this organocatalyst can be an alternative to piperidine for organic transformations.

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)0.000
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 score0.008
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
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 head0.198
Teacher spread0.181 · 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