Synthesis of Pyrazolyl-2-pyrazolines by Treatment of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones with Hydrazine and Their Oxidation to Bis(pyrazoles)
Albert Lévai
1
,
Artur C. Silva
2
,
Diana Pinto
2
,
José A. S. Cavaleiro
2
,
Ibon Alkorta
3
,
José Elguero
3
,
József Jekő
4
4
ICN Hungary Co., Ltd., 4440 Tiszavasvári, Hungary
|
Publication type: Journal Article
Publication date: 2004-11-02
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The synthesis of several 1-acetyl-3-aryl-5-[3-(2-hydroxyphenyl)pyrazol-4-yl]-2-pyrazolines 3a−3h has been accomplished by treatment of the 3-(3-aryl-3-oxopropenyl)chromen4-ones 1a−h with hydrazine hydrate in hot acetic acid. The 1acetyl-3-aryl-5-(3-chromonyl)-2-pyrazolines 2a−2f were also obtained as by-products. Oxidation of the 1-acetyl-4-pyrazolyl-2-pyrazolines 3a−3f with DDQ gave the 3(5)-aryl-5(3)-[3(2-hydroxyphenyl)pyrazol-4-yl]pyrazoles 5a−5f. The oxidation of the 2-pyrazoline rings was accompanied by N-deacylation. The reaction mechanisms of both transformations are discussed, the first one being supported by experimental re
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GOST
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Lévai A. et al. Synthesis of Pyrazolyl-2-pyrazolines by Treatment of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones with Hydrazine and Their Oxidation to Bis(pyrazoles) // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 22. pp. 4672-4679.
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Lévai A., Silva A. C., Pinto D., Cavaleiro J. A. S., Alkorta I., Elguero J., Jekő J. Synthesis of Pyrazolyl-2-pyrazolines by Treatment of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones with Hydrazine and Their Oxidation to Bis(pyrazoles) // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 22. pp. 4672-4679.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.200400465
UR - https://doi.org/10.1002/ejoc.200400465
TI - Synthesis of Pyrazolyl-2-pyrazolines by Treatment of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones with Hydrazine and Their Oxidation to Bis(pyrazoles)
T2 - European Journal of Organic Chemistry
AU - Lévai, Albert
AU - Silva, Artur C.
AU - Pinto, Diana
AU - Cavaleiro, José A. S.
AU - Alkorta, Ibon
AU - Elguero, José
AU - Jekő, József
PY - 2004
DA - 2004/11/02
PB - Wiley
SP - 4672-4679
IS - 22
VL - 2004
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2004_Lévai,
author = {Albert Lévai and Artur C. Silva and Diana Pinto and José A. S. Cavaleiro and Ibon Alkorta and José Elguero and József Jekő},
title = {Synthesis of Pyrazolyl-2-pyrazolines by Treatment of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones with Hydrazine and Their Oxidation to Bis(pyrazoles)},
journal = {European Journal of Organic Chemistry},
year = {2004},
volume = {2004},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ejoc.200400465},
number = {22},
pages = {4672--4679},
doi = {10.1002/ejoc.200400465}
}
Cite this
MLA
Copy
Lévai, Albert, et al. “Synthesis of Pyrazolyl-2-pyrazolines by Treatment of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones with Hydrazine and Their Oxidation to Bis(pyrazoles).” European Journal of Organic Chemistry, vol. 2004, no. 22, Nov. 2004, pp. 4672-4679. https://doi.org/10.1002/ejoc.200400465.