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Advances in Heterocyclic Aromatic Construction

2015· book-chapter· en· W3100612338 on OpenAlexaboutno aff
Tristan H. Lambert

Bibliographic record

VenueOxford University Press eBooks · 2015
Typebook-chapter
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsnot available
Fundersnot available
KeywordsFuranChemistryPyrroleCarbeneCatalysisPolymer chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Rubén Vicente and Luis A. López at the University of Oviedo in Spain reported (Angew. Chem. Int. Ed. 2012, 51, 8063) the synthesis of cyclopropyl furan 2 from alkylidene 1 and styrene by way of a zinc carbene intermediate. The same substrate 1 was also converted (Angew. Chem. Int. Ed. 2012, 51, 12128) to furan 3 via catalysis with tetrahydrothiophene in the presence of benzoic acid by J. Stephen Clark at the University of Glasgow. Xue-Long Hou at the Shanghai Institute of Organic Chemistry discovered (Org. Lett. 2012, 14, 5756) that palladacycle 6 catalyzes the conversion of bicyclic alkene 4 and alkynone 5 to furan 7. A silver-mediated C–H/C–H functionalization strategy for the synthesis of furan 9 from alkyne 8 and ethyl acetoacetate was developed (J. Am. Chem. Soc. 2012, 134, 5766) by Aiwen Lei at Wuhan University. Ning Jiao at Peking University and East China Normal University found (Org. Lett. 2012, 14, 4926) that azide 10 and aldehyde 11 could be converted to either pyrrole 12 or 13 with complete regiocontrol by judicious choice of a metal catalyst. Meanwhile, Michael A. Kerr at the University of Western Ontario developed (Angew. Chem. Int. Ed. 2012, 51, 11088) a multicomponent synthesis of pyrrole 16 involving the merger of nitrone 14 and the donor–acceptor cyclopropane 15. The pyrrole 16 was subsequently converted to an intermediate in the synthesis of the cholesterol-lowering drug compound Lipitor. A robust synthesis of the ynone trifluoroboronate 17 was developed (Org. Lett. 2012, 14, 5354) by James D. Kirkham and Joseph P.A. Harrity at the University of Sheffield, which thus allowed for the ready production of trifluoroboronate-substituted pyrazole 18. An alternative pyrazole synthesis via oxidative closure of unsaturated hydrazine 19 to produce 20 was reported (Org. Lett. 2012, 14, 5030) by Yu Rao at Tsinghua University. A unique fluoropyrazole construction was developed (Angew. Chem. Int. Ed. 2012, 51, 12059) by Junji Ichikawa at the University of Tsukuba that involved nucleophilic substitution of two of the fluorides in 21 to form pyrazole 22.

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.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Review · Consensus signal: Review
Teacher disagreement score0.008
Threshold uncertainty score0.028

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.001
Science and technology studies0.0010.001
Scholarly communication0.0010.001
Open science0.0010.001
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0080.004

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 head0.023
GPT teacher head0.215
Teacher spread0.192 · 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

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
Domainnot available
GenreReview

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations0
Published2015
Admission routes1
Has abstractyes

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