Evidence map›Paper›PMID 31291500›Full record

ArticleAngewandte Chemie (International ed. in English)2019

Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane.

Nisalak Trongsiriwat, Youge Pu, Yexenia Nieves-Quinones, Russell A Shelp, Marisa C Kozlowski, Patrick J Walsh

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.

0numbers the graph read from it
0cells of the map it votes in
12citing 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

12 citing papers in PubMed.

  1. Bicyclo[1.1.1]pentane Ketones via Friedel-Crafts Acylation.The Journal of organic chemistry · 2026
    Article
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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.

Nisalak TrongsiriwatRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.ORCID 0000-0002-8582-1750
Youge PuRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
Yexenia Nieves-QuinonesRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
Russell A ShelpRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
Marisa C KozlowskiRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
Patrick J WalshRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.ORCID 0000-0001-8392-4150

Funding

Computation and Development of New, Enabling Synthetic MethodsR35GM131902 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI Marisa C Kozlowski · 2019 to 2026
$4.5M
Computational Methods for Selective CatalysisR01GM087605 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI KOZLOWSKI, MARISA C · 2010 to 2019
$2.4M
Department of Chemistry, University of Pennsylvania CHE-1464744NIGMS NIH HHS R01 GM087605NIGMS NIH HHS R35 GM131902NIH HHS GM131902XSEDE TG-CHE120052
6 · The paper itself

Abstract

Bicyclo[1.1.1]pentanes (BCPs) have sparked the interest of medicinal chemists due to their recent discovery as bioisosteres of aromatic rings. To study the biological activity of this relatively new class of bioisosteres, reliable methods to incorporate BCPs into target molecules are in high demand, as reflected by a flurry of methods for BCP synthesis in recent years. In this work, we disclose a general method for the synthesis of BCP-containing dithianes which, upon deprotection, provide access to BCP analogues of medicinally abundant diarylketones. A broad scope of 2-aryl-1,3-dithianes, including several heterocyclic derivatives, react with [1.1.1]propellane to afford 26 new derivatives in good to excellent yields. Further transformation of the dithiane portion into a variety of functional groups demonstrates the robustness of the products. A computational study indicates that the reaction of 2-aryl-1,3-dithianes and [1.1.1]propellane proceeds via a two-electron pathway.

Indexed as

Heterocyclic CompoundsMolecular Structure1,3-dithianeHeterocyclic Compoundsbioisosteresketonespropellanessynthetic methodsumpolung

Identifiers

PMID31291500
PMCPMC6788743

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.