Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles
Publication type: Journal Article
Publication date: 2022-04-08
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
35394780
Organic Chemistry
Abstract
An interaction of 1,5-diaryl-3-X-pent-4-yn-1-ones (where X stands for piperidin-1-yl, morpholin-4-yl, 4-methylpiperazin-1-yl) with arylhydrazines proceeds at room temperature and results in 3-aryl-5-arylethynyl-1-phenyl-4,5-dihydro-1H-pyrazoles with up to 57-73% yields. Under similar conditions, the cyclocondensation of conjugated 2,4,1-enynones with arylhydrazine proceeds only in the presence of cyclic amines. 1,5-Diaryl-3-X-pent-4-yn-1-ones are reported as synthetic equivalents of conjugated 2,4,1-enynones in reactions with arylhydrazines. On the basis of obtained data, there are highly efficient methods developed for the synthesis of 5-arylethynyl-substituted 4,5-dihydro-1H-pyrazoles, as well as for similarly structured 1H-pyrazoles prepared by oxidation in AcOH. Presented products possess quite marked fluorescent abilities. Emission maximum wavelengths are located at 453-465 and 363-400 nm, respectively; certain compounds show extremely large Stokes shifts that may reach 91,000 cm-1.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Russian Chemical Bulletin
2 publications, 15.38%
|
|
|
Tetrahedron
2 publications, 15.38%
|
|
|
Molecular Catalysis
1 publication, 7.69%
|
|
|
RSC Advances
1 publication, 7.69%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 7.69%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 7.69%
|
|
|
Journal of Organic Chemistry
1 publication, 7.69%
|
|
|
Synthesis
1 publication, 7.69%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 7.69%
|
|
|
Russian Journal of Organic Chemistry
1 publication, 7.69%
|
|
|
Журнал органической химии
1 publication, 7.69%
|
|
|
1
2
|
Publishers
|
1
2
3
4
|
|
|
Elsevier
4 publications, 30.77%
|
|
|
Royal Society of Chemistry (RSC)
2 publications, 15.38%
|
|
|
Springer Nature
2 publications, 15.38%
|
|
|
Wiley
1 publication, 7.69%
|
|
|
American Chemical Society (ACS)
1 publication, 7.69%
|
|
|
Georg Thieme Verlag KG
1 publication, 7.69%
|
|
|
Pleiades Publishing
1 publication, 7.69%
|
|
|
The Russian Academy of Sciences
1 publication, 7.69%
|
|
|
1
2
3
4
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
13
Total citations:
13
Citations from 2024:
6
(46.15%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Odin I. S. et al. Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles // Journal of Organic Chemistry. 2022. Vol. 87. No. 9. pp. 5916-5924.
GOST all authors (up to 50)
Copy
Odin I. S., Chertov A. Yu., Grigoreva O. B., Golovanov A. A. Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles // Journal of Organic Chemistry. 2022. Vol. 87. No. 9. pp. 5916-5924.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.2c00198
UR - https://doi.org/10.1021/acs.joc.2c00198
TI - Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles
T2 - Journal of Organic Chemistry
AU - Odin, Ivan S.
AU - Chertov, Anton Yu
AU - Grigoreva, Olga B
AU - Golovanov, A A
PY - 2022
DA - 2022/04/08
PB - American Chemical Society (ACS)
SP - 5916-5924
IS - 9
VL - 87
PMID - 35394780
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Odin,
author = {Ivan S. Odin and Anton Yu Chertov and Olga B Grigoreva and A A Golovanov},
title = {Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.2c00198},
number = {9},
pages = {5916--5924},
doi = {10.1021/acs.joc.2c00198}
}
Cite this
MLA
Copy
Odin, Ivan S., et al. “Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles.” Journal of Organic Chemistry, vol. 87, no. 9, Apr. 2022, pp. 5916-5924. https://doi.org/10.1021/acs.joc.2c00198.