Regiochemical Control of Pyrazoles by Solvent and β-Enamino Diketone Structure: Regioselective Synthesis of 4,5-Disubstituted N -Phenylpyrazoles
Thiago F Souza
1
,
Michael J V Silva
1
,
Raí G M Silva
1
,
Davana S Gonçalves
1
,
Paula A Simon
1
,
Andrey P Jacomini
1
,
Ernani Abicht Basso
1
,
Sidnei Moura
2
,
Marcos A. P. Martins
3
,
Davi F Back
3
,
Fernanda Rosa
1
Тип публикации: Journal Article
Дата публикации: 2017-03-13
scimago Q2
wos Q2
БС1
SJR: 0.542
CiteScore: 5.0
Impact factor: 2.7
ISSN: 21935807, 21935815
Organic Chemistry
Краткое описание
A simple method for the regiocontrolled synthesis of the 4,5-disubstituted N-phenylpyrazole regioisomers 2 and 3 from β-enamino diketones and phenylhydrazine is described. Pyrazole 2 was prepared regioselectively by carrying out the reaction in a protic solvent, whereas pyrazole 3 was obtained as the main product by using an aprotic solvent. Steric factors regarding the β-enamino diketones also influenced the regiochemistry of 2 and 3. The influence of solvent on the reaction outcome can be rationalized by using Fukui indices. The structures of 2 and 3 were unambiguously elucidated by 1H and 13C NMR spectroscopy, two-dimensional HMBC experiments, high resolution mass spectrometry, and X-ray crystallographic analysis.
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Souza T. F. et al. Regiochemical Control of Pyrazoles by Solvent and β-Enamino Diketone Structure: Regioselective Synthesis of 4,5-Disubstituted N -Phenylpyrazoles // Asian Journal of Organic Chemistry. 2017. Vol. 6. No. 5. pp. 627-633.
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Souza T. F., Silva M. J. V., Silva R. G. M., Gonçalves D. S., Simon P. A., Jacomini A. P., Basso E. A., Moura S., Martins M. A. P., Back D. F., Rosa F. Regiochemical Control of Pyrazoles by Solvent and β-Enamino Diketone Structure: Regioselective Synthesis of 4,5-Disubstituted N -Phenylpyrazoles // Asian Journal of Organic Chemistry. 2017. Vol. 6. No. 5. pp. 627-633.
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TY - JOUR
DO - 10.1002/ajoc.201700048
UR - https://doi.org/10.1002/ajoc.201700048
TI - Regiochemical Control of Pyrazoles by Solvent and β-Enamino Diketone Structure: Regioselective Synthesis of 4,5-Disubstituted N -Phenylpyrazoles
T2 - Asian Journal of Organic Chemistry
AU - Souza, Thiago F
AU - Silva, Michael J V
AU - Silva, Raí G M
AU - Gonçalves, Davana S
AU - Simon, Paula A
AU - Jacomini, Andrey P
AU - Basso, Ernani Abicht
AU - Moura, Sidnei
AU - Martins, Marcos A. P.
AU - Back, Davi F
AU - Rosa, Fernanda
PY - 2017
DA - 2017/03/13
PB - Wiley
SP - 627-633
IS - 5
VL - 6
SN - 2193-5807
SN - 2193-5815
ER -
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BibTex (до 50 авторов)
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@article{2017_Souza,
author = {Thiago F Souza and Michael J V Silva and Raí G M Silva and Davana S Gonçalves and Paula A Simon and Andrey P Jacomini and Ernani Abicht Basso and Sidnei Moura and Marcos A. P. Martins and Davi F Back and Fernanda Rosa},
title = {Regiochemical Control of Pyrazoles by Solvent and β-Enamino Diketone Structure: Regioselective Synthesis of 4,5-Disubstituted N -Phenylpyrazoles},
journal = {Asian Journal of Organic Chemistry},
year = {2017},
volume = {6},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/ajoc.201700048},
number = {5},
pages = {627--633},
doi = {10.1002/ajoc.201700048}
}
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MLA
Скопировать
Souza, Thiago F., et al. “Regiochemical Control of Pyrazoles by Solvent and β-Enamino Diketone Structure: Regioselective Synthesis of 4,5-Disubstituted N -Phenylpyrazoles.” Asian Journal of Organic Chemistry, vol. 6, no. 5, Mar. 2017, pp. 627-633. https://doi.org/10.1002/ajoc.201700048.