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Record W3163761805 · doi:10.1039/d1cc02245h

Constructing fused N-heterocycles from unprotected mesoionic N-heterocyclic olefins and organic azides <i>via</i> diazo transfer

2021· article· en· W3163761805 on OpenAlex
Qiuming Liang, Kasumi Hayashi, Yimin Zeng, José L. Jiménez-Santiago, Datong Song

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

VenueChemical Communications · 2021
Typearticle
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsUniversity of TorontoToronto Public Health
FundersNatural Sciences and Engineering Research Council of CanadaConsejo Nacional de Ciencia y Tecnología
KeywordsMesoionicDiazoChemistryCombinatorial chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Mesoionic N-heterocyclic olefins (mNHOs) were first reported last year and their reactivity remains largely unexplored. Herein we report the reaction of unprotected mNHOs and organic azides as a novel synthetic route to a variety of pyrazolo[3,4-d][1,2,3]triazoles, an important structural motif in drug candidates and energetic materials. The only byproduct aniline can be easily recycled and converted back to the starting organic azide, in compliance with the green chemistry principle. The reaction mechanism has been explored through experimental and computational studies.

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 categoriesMeta-epidemiology (narrow)
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 score0.012
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.001
Research integrity0.0000.001
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 head0.020
GPT teacher head0.231
Teacher spread0.211 · 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