Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines
Publication type: Journal Article
Publication date: 2018-06-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29916705
Organic Chemistry
Abstract
A high yield synthesis of 1,2-dihydropyrimidines by the Rh(II)-catalyzed reaction of diazocarbonyl compounds with 1,4-di- and 1,4,5-trisubstituted pyrazoles is reported. This reaction represents the first example of a carbenoid insertion into a N-N bond and provides a novel approach to 4-unsubstituted 1,2-dihydropyrimidines with a broad range of functional group tolerance. According to DFT calculations, the pyrazole ring expansion proceeds via the sequential formation of the metal-bound pyrazolium ylide, metal-free pyrazolium ylide, and 1,5-diazahexatriene followed by 1,6-cyclization.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
|
|
|
Organic Letters
3 publications, 7.5%
|
|
|
Organic Chemistry Frontiers
3 publications, 7.5%
|
|
|
Chemistry - A European Journal
3 publications, 7.5%
|
|
|
Synthesis
3 publications, 7.5%
|
|
|
European Journal of Organic Chemistry
2 publications, 5%
|
|
|
Asian Journal of Organic Chemistry
2 publications, 5%
|
|
|
Angewandte Chemie - International Edition
2 publications, 5%
|
|
|
Angewandte Chemie
2 publications, 5%
|
|
|
ACS Omega
1 publication, 2.5%
|
|
|
Mini-Reviews in Medicinal Chemistry
1 publication, 2.5%
|
|
|
Chinese Journal of Organic Chemistry
1 publication, 2.5%
|
|
|
Organics
1 publication, 2.5%
|
|
|
Coordination Chemistry Reviews
1 publication, 2.5%
|
|
|
Trends in Chemistry
1 publication, 2.5%
|
|
|
Journal of the American Chemical Society
1 publication, 2.5%
|
|
|
Journal of Organic Chemistry
1 publication, 2.5%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 2.5%
|
|
|
New Journal of Chemistry
1 publication, 2.5%
|
|
|
Advanced Science
1 publication, 2.5%
|
|
|
Journal of Heterocyclic Chemistry
1 publication, 2.5%
|
|
|
Chinese Journal of Chemistry
1 publication, 2.5%
|
|
|
Russian Journal of Organic Chemistry
1 publication, 2.5%
|
|
|
Accounts of Chemical Research
1 publication, 2.5%
|
|
|
Журнал органической химии
1 publication, 2.5%
|
|
|
Nature Communications
1 publication, 2.5%
|
|
|
Chemical Reviews
1 publication, 2.5%
|
|
|
Chemical Communications
1 publication, 2.5%
|
|
|
1
2
3
|
Publishers
|
2
4
6
8
10
12
14
|
|
|
Wiley
14 publications, 35%
|
|
|
American Chemical Society (ACS)
8 publications, 20%
|
|
|
Royal Society of Chemistry (RSC)
6 publications, 15%
|
|
|
Elsevier
3 publications, 7.5%
|
|
|
Georg Thieme Verlag KG
3 publications, 7.5%
|
|
|
Bentham Science Publishers Ltd.
1 publication, 2.5%
|
|
|
Shanghai Institute of Organic Chemistry
1 publication, 2.5%
|
|
|
MDPI
1 publication, 2.5%
|
|
|
Pleiades Publishing
1 publication, 2.5%
|
|
|
The Russian Academy of Sciences
1 publication, 2.5%
|
|
|
Springer Nature
1 publication, 2.5%
|
|
|
2
4
6
8
10
12
14
|
- 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
40
Total citations:
40
Citations from 2024:
18
(45%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Koronatov A. N. et al. Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines // Journal of Organic Chemistry. 2018. Vol. 83. No. 16. pp. 9210-9219.
GOST all authors (up to 50)
Copy
Koronatov A., Koronatov A. N., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines // Journal of Organic Chemistry. 2018. Vol. 83. No. 16. pp. 9210-9219.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.8b01228
UR - https://pubs.acs.org/doi/10.1021/acs.joc.8b01228
TI - Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines
T2 - Journal of Organic Chemistry
AU - Koronatov, Aleksandr
AU - Koronatov, Alexander N
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2018
DA - 2018/06/19
PB - American Chemical Society (ACS)
SP - 9210-9219
IS - 16
VL - 83
PMID - 29916705
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Koronatov,
author = {Aleksandr Koronatov and Alexander N Koronatov and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.8b01228},
number = {16},
pages = {9210--9219},
doi = {10.1021/acs.joc.8b01228}
}
Cite this
MLA
Copy
Koronatov, Alexander N., et al. “Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines.” Journal of Organic Chemistry, vol. 83, no. 16, Jun. 2018, pp. 9210-9219. https://pubs.acs.org/doi/10.1021/acs.joc.8b01228.