Evidence map›Paper›PMID 35340781›Full record

ArticleChemistry of heterocyclic compounds2022

Expanding the chemical space of 3(5)-functionalized 1,2,4-triazoles.

Dmytro M Khomenko, Roman O Doroshchuk, Yulia M Ohorodnik, Hanna V Ivanova, Borys V Zakharchenko, Ilona V Raspertova, Oleksandr V Vaschenko, Alexey V Dobrydnev, Oleksandr O Grygorenko, Rostyslav D Lampeka

Open access · bronzeAbstract read
In one paragraph

Article in Chemistry of heterocyclic compounds, 2022. 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
1.9field-weighted citation impact, top 16% 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

4 citing papers in PubMed, 18 citations in OpenAlex.

  1. Synthesis, structures and Hirshfeld surface analyses of 2-hy-droxy-Acta crystallographica. Section E, Crystallographic communications · 2024
    Article
  2. Synthesis and crystal structure ofActa crystallographica. Section E, Crystallographic communications · 2024
    Article
  3. Crystal structure and Hirshfeld-surface analysis of di-aqua-bis-(5-methyl-1Acta crystallographica. Section E, Crystallographic communications · 2024
    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

10 authors at 2 institutions in 1 country.

Dmytro M KhomenkoEnamine Ltd., 78 Chervonotkatska St., Kyiv, 02094 Ukraine.
Roman O DoroshchukEnamine Ltd., 78 Chervonotkatska St., Kyiv, 02094 Ukraine.
Yulia M OhorodnikTaras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601 Ukraine.
Hanna V IvanovaTaras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601 Ukraine.
Borys V ZakharchenkoEnamine Ltd., 78 Chervonotkatska St., Kyiv, 02094 Ukraine.
Ilona V RaspertovaTaras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601 Ukraine.
Oleksandr V VaschenkoTaras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601 Ukraine.
Alexey V DobrydnevEnamine Ltd., 78 Chervonotkatska St., Kyiv, 02094 Ukraine.
Oleksandr O GrygorenkoEnamine Ltd., 78 Chervonotkatska St., Kyiv, 02094 Ukraine.
Rostyslav D LampekaTaras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601 Ukraine.
Taras Shevchenko National University of Kyiv · UAEnamine (Ukraine) · UA

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

An efficient approach to the gram-scale synthesis of 3(5)-substituted, 1,3- and 1,5-disubstituted 1,2,4-triazole-derived building blocks is described. The key synthetic precursors - 1,2,4-triazole-3(5)-carboxylates (20 examples, 35-89% yield) were prepared from readily available acyl hydrazides and ethyl 2-ethoxy-2-iminoacetate hydrochloride. Further transformations were performed following the convergent synthetic strategy and allowed the preparation of 1,3- and 1,5-disubstituted 1,2,4-triazole-derived esters (16 examples, 25-75% yield), 3(5)-substituted, 1,3- and 1,5-disubstituted carboxylate salts (18 examples, 78-93% yield), amides (5 examples, 82-93% yield), nitriles (5 examples, 30-85% yield), hydrazides (6 examples, 84-89% yield), and hydroxamic acids (3 examples, 73-78% yield). Considering wide applications of the 1,2,4-triazole motif in medicinal chemistry, these compounds are valuable building blocks for lead-oriented synthesis; they have also great potential for coordination chemistry. Supplementary Information: The online version contains supplementary material available at 10.1007/s10593-022-03064-z.

Indexed as

1,2,4-triazolesacyl hydrazidesalkylationcyclizationfunctional groupsregioisomers

Identifiers

PMID35340781
PMCPMC8940976
OpenAlexW4221136498

What OpenQuestion holds

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Registered trials

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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.