Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles
Publication type: Journal Article
Publication date: 2018-10-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract A novel effective method is reported for the preparation of 1-amino-1H-pyrazole-4-carboxylic acid derivatives by Fe(II)-catalyzed rearrangement of isoxazoles having (2,4-dinitrophenylhydrazono)methyl substituent at C4. The reaction proceeds smoothly for both E and Z isomers of 4-(hydrazonomethyl)isoxazoles, and this means it is not necessary to separate mixtures of E/Z-isomers of the hydrazones prepared by reaction of 5-methoxy/pirrolidino-4-carbonylisoxazoles and 2,4-dinitrophenylhydrazine. The rearrangement proceeds via the formation of an aziridine intermediate which can be isolated in certain cases. The 2-nitro group in the synthesized 1-[(2,4-dinitrophenyl)amino]-1H-pyrazole-4-carboxylic esters can be selectively reduced in two steps via acylation of the amino group followed by hydrogenation-deacylation using H2-Pd/C.
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13
Total citations:
13
Citations from 2024:
3
(23%)
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GOST
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Galenko E. E. et al. Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles // Tetrahedron. 2018. Vol. 74. No. 43. pp. 6288-6298.
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Galenko E. E., Ivanov V. A., Novikov M. S., Zolotarev A. A., Khlebnikov A. F. Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles // Tetrahedron. 2018. Vol. 74. No. 43. pp. 6288-6298.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2018.09.015
UR - https://doi.org/10.1016/j.tet.2018.09.015
TI - Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles
T2 - Tetrahedron
AU - Galenko, Ekaterina E
AU - Ivanov, Viktor A.
AU - Novikov, Mikhail S.
AU - Zolotarev, A. A.
AU - Khlebnikov, Alexander F
PY - 2018
DA - 2018/10/01
PB - Elsevier
SP - 6288-6298
IS - 43
VL - 74
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2018_Galenko,
author = {Ekaterina E Galenko and Viktor A. Ivanov and Mikhail S. Novikov and A. A. Zolotarev and Alexander F Khlebnikov},
title = {Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles},
journal = {Tetrahedron},
year = {2018},
volume = {74},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.tet.2018.09.015},
number = {43},
pages = {6288--6298},
doi = {10.1016/j.tet.2018.09.015}
}
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MLA
Copy
Galenko, Ekaterina E., et al. “Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles.” Tetrahedron, vol. 74, no. 43, Oct. 2018, pp. 6288-6298. https://doi.org/10.1016/j.tet.2018.09.015.