A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles
Daniel R Fandrick
1
,
Sanjit Sanyal
1
,
Joseph Kaloko
1
,
Jan Mulder
1
,
Yuwen Wang
1
,
Linglin Wu
1
,
HeeWon Lee
1
,
Frank Roschangar
1
,
Matthias Hoffmann
2
,
Chris H. Senanayake
1
1
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States
|
Publication type: Journal Article
Publication date: 2015-06-01
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
26030838
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A Michael equilibration model is presented to provide for site-selective pyrazole condensations between alkoxyacrylonitriles and hydrazines. Both pyrazole isomers were accessed with high selectivity by employment of kinetically or thermodynamically controlled conditions. Substrate scope and identification of Michael intermediates, as well as competitive pathways, support the presented mechanistic proposal. Sandmeyer derivatization provided site-selective access to fully substituted pyrazoles.
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Total citations:
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Citations from 2025:
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(10.52%)
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GOST
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Fandrick D. R. et al. A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles // Organic Letters. 2015. Vol. 17. No. 12. pp. 2964-2967.
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Fandrick D. R., Sanyal S., Kaloko J., Mulder J., Wang Y., Wu L., Lee H., Roschangar F., Hoffmann M., Senanayake C. H. A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles // Organic Letters. 2015. Vol. 17. No. 12. pp. 2964-2967.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.5b01248
UR - https://doi.org/10.1021/acs.orglett.5b01248
TI - A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles
T2 - Organic Letters
AU - Fandrick, Daniel R
AU - Sanyal, Sanjit
AU - Kaloko, Joseph
AU - Mulder, Jan
AU - Wang, Yuwen
AU - Wu, Linglin
AU - Lee, HeeWon
AU - Roschangar, Frank
AU - Hoffmann, Matthias
AU - Senanayake, Chris H.
PY - 2015
DA - 2015/06/01
PB - American Chemical Society (ACS)
SP - 2964-2967
IS - 12
VL - 17
PMID - 26030838
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Fandrick,
author = {Daniel R Fandrick and Sanjit Sanyal and Joseph Kaloko and Jan Mulder and Yuwen Wang and Linglin Wu and HeeWon Lee and Frank Roschangar and Matthias Hoffmann and Chris H. Senanayake},
title = {A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.5b01248},
number = {12},
pages = {2964--2967},
doi = {10.1021/acs.orglett.5b01248}
}
Cite this
MLA
Copy
Fandrick, Daniel R., et al. “A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles.” Organic Letters, vol. 17, no. 12, Jun. 2015, pp. 2964-2967. https://doi.org/10.1021/acs.orglett.5b01248.