Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines
Тип публикации: Journal Article
Дата публикации: 2018-06-19
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
29916705
Organic Chemistry
Краткое описание
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.
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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.
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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.
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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 -
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@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}
}
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MLA
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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.
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