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Record W2038216881 · doi:10.1002/adsc.200700500

Efficient Preparation of the Isoindoline Framework <i>via</i> a Six Component, Tandem Double A<sup>3</sup>‐Coupling and [2+2+2] Cycloaddition Reaction

2008· article· en· W2038216881 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.

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

Bibliographic record

VenueAdvanced Synthesis & Catalysis · 2008
Typearticle
Languageen
FieldChemistry
TopicSynthesis and pharmacology of benzodiazepine derivatives
Canadian institutionsMcGill University
FundersNatural Sciences and Engineering Research Council of CanadaCanada Research Chairs
KeywordsCycloadditionIsoindolineChemistryAlkyneTandemAldehydeCatalysisAmine gas treatingCombinatorial chemistryCascade reactionBromideCoupling reactionOrganic chemistry

Abstract

fetched live from OpenAlex

Abstract The preparation of tetrasubstituted isoindolines from three alkyne units, two aldehyde units and a primary amine via three consecutive reactions, two aldehyde‐amine‐alkyne couplings (A 3 ‐couplings) and a final [2+2+2] cycloaddition, in a single synthetic operation, is described. The A 3 ‐couplings are catalyzed by copper bromide and the cycloaddition is catalyzed by Wilkinson’s catalyst. It was found that many catalysts known to be efficient at the cycloaddition step were not suitable when this step was part of the tandem reaction sequence. Wilkinson’s catalyst was found to be unique in its suitability for the overall domino reaction sequence.

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 score0.047
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 studies0.0010.000
Scholarly communication0.0000.000
Open science0.0000.000
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 head0.016
GPT teacher head0.270
Teacher spread0.254 · 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