Evidence map›Paper›PMID 33978029›Full record

ArticleOrganic & biomolecular chemistry2021

A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[

Christopher Cunningham, Matthew Cloyd, Aimee Phillips, Soha Khan, Katherine Whalen, Tanay Kesharwani

Open access · greenAbstract read
In one paragraph

Article in Organic & biomolecular chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
0.5field-weighted citation impact, top 41% of its field
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

2 citing papers in PubMed, 7 citations in OpenAlex.

  1. Article
  2. Synthesis of Benzo[The Journal of organic chemistry · 2022
    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

6 authors at 1 institution in 1 country.

Christopher CunninghamDepartment of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA. tkesharwani@uwf.edu.
Matthew CloydDepartment of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA. tkesharwani@uwf.edu.
Aimee PhillipsDepartment of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA. tkesharwani@uwf.edu.
Soha KhanDepartment of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA. tkesharwani@uwf.edu.
Katherine WhalenDepartment of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA. tkesharwani@uwf.edu.
Tanay KesharwaniDepartment of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, Fl 32514, USA. tkesharwani@uwf.edu.ORCID 0000-0001-8193-0004
Pensacola Historical Society · US

Funding

MARC at University of West FloridaT34GM110517 · NIGMS · UNIVERSITY OF WEST FLORIDA · PI CAVNAR, PETER J., MOLEK, KAREN SINCLAIR · 2014 to 2023
$2.6M
NIGMS NIH HHS T34 GM110517
6 · The paper itself

Abstract

In this study, a new environmentally benign iodine-mediated one-pot iodocyclization/alkylation strategy for the synthesis of benzo[b]thiophene derivatives starting from 2-alkynylthioanisoles was developed. The synthesis of a diverse population of 2,3-disubstituted benzo[b]thiophenes was achieved in high yields by employing moderate reaction conditions using 1,3-dicarbonyl substrates as the nucleophile and various substituted propargyl alcohols as both the cyclization precursor and the alkylating agent. This method resulted in the formation of a series of complex structures obtained in a single step. Additionally, a strategy was devised for the one pot iodocyclization/oxidation of propargyl alcohols into carbonyl functionalized benzo[b]thiophene structures. These green one-pot reaction processes were designed to reduce wastes and byproducts while generating a complex substitution pattern on the benzo[b]thiophene structure. The reported methodologies may be used to synthesize more functionalized benzo[b]thiophene structures that can be used in both biomedical and organic electronic applications.

Indexed as

ThiophenesAlkylationCyclizationMolecular StructurebenzothiopheneThiophenes

Identifiers

PMID33978029
PMCPMC8211089
OpenAlexW3153182327

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.