Evidence map›Paper›PMID 26576646›Full record

ArticleChemical communications (Cambridge, England)2016

Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles.

Qian Gao, Wen-Juan Hao, Feng Liu, Shu-Jiang Tu, Shu-Liang Wang, Guigen Li, Bo Jiang

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical communications (Cambridge, England), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

4 citing papers in PubMed.

  1. Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-Beilstein journal of organic chemistry · 2024
    Article
  2. Article
  3. Article
  4. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

7 authors.

Qian GaoSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Wen-Juan HaoSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Feng LiuSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Shu-Jiang TuSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Shu-Liang WangSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Guigen LiInstitute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University, Nanjing 210093, P. R. China and Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. guigen.li@ttu.edu.cn.
Bo JiangSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.

Funding

GAP Chemistry Approaches to Chiral Amino Acids, Peptides and PeptidomimeticsR33DA031860 · NIDA · TEXAS TECH UNIVERSITY · PI LI, GUIGEN · 2013 to 2014
$706k
NIDA NIH HHS R33 DA031860NIDA NIH HHS R33DA031860
6 · The paper itself

Abstract

A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels-Alder reaction sequence, resulting in continuous multiple bond-forming events including C-N, C-O and C-H bonds to rapidly build up molecular complexity.

Indexed as

AcrylatesCrystallography, X-RayCyanidesCyclizationDicarboxylic AcidsImidesModels, MolecularMolecular StructurePyransStereoisomerismAcrylatesacrylic acidCyanidesDicarboxylic AcidsImidesPyrans

Identifiers

PMID26576646
PMCPMC4703471

What OpenQuestion holds

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.