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Record W2088396801 · doi:10.1002/jhet.5570440610

Synthesis of novel coumarin and benzocoumarin derivatives and their biological and photophysical studies

2007· article· en· W2088396801 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.

Bibliographic record

VenueJournal of Heterocyclic Chemistry · 2007
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Biological Evaluation
Canadian institutionsUniversité de SherbrookeUniversity of WinnipegUniversity of British Columbia, Okanagan CampusUniversity of British Columbia
Fundersnot available
KeywordsChemistryCoumarinNucleophileRing (chemistry)MethyleneFluorescenceProton NMRMedicinal chemistryNucleophilic substitutionStereochemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Abstract magnified image Several derivatives of coumarin‐3 N ‐carboxamides ( 3‐21 ) have been prepared via the reaction of the coumarin‐3‐carbonyl chloride ( 1 ) with a number of nucleophiles. Novel double‐headed coumarin‐3 N ‐carboxamides ( 26‐33 ) were also produced using the same method. The Pechmann‐Duisberg reaction was applied to prepare new benzo[ f ]‐ benzo[ h ]coumarins and 4‐(chloromethyl)‐pyrano[3,2‐ c ]coumarin‐2‐one ( 36‐42 ). The reaction of 1‐chloromethylbenzo[ f ]coumarins ( 36 ) with cyanide anion under different reaction conditions was also investigated in order to assess its suitability for nucleophilic substitution reactions as well as ring transformation products ( 43‐49 ). Synthesis of 1‐((benzo[ d ]thiazol‐2‐yl)methyl)‐9‐hydroxybenzo[ f ]coumarin ( 50 ) represented the first example of methylene bridge‐head heterocyclecontaining benzo[ f ]coumarin. Some of the newly prepared coumarins exhibited anti‐bacterial activity against Gram Positive and Gram negative bacteria. Compound 36d was found to be active against all the screened bacteria. Photophysical studies were performed on selected fluorescent benzo[ f ]‐ and benzo[ h ]coumarin and the quantum yields were also calculated. All new compounds were characterized by IR, MS, 1 H and 13 C NMR, as well as elemental analysis.

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)0.001
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 score0.029
Threshold uncertainty score0.441

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
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)0.0000.000

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 head0.065
GPT teacher head0.310
Teacher spread0.245 · 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