Isoxazole strategy for the synthesis of α-aminopyrrole derivatives
Publication type: Journal Article
Publication date: 2019-08-06
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31385507
Organic Chemistry
Abstract
A synthesis of methyl 5-aminopyrrole-3-carboxylates from 4-methyleneisoxazol-3-ones via "cyanide Michael addition/methylation/reductive isoxazole-pyrrole transformation" is developed. The last step occurs in a domino mode involving Mo(CO)6-mediated reductive isoxazole ring-opening, Mo(CO)6-catalyzed cis-trans-isomerization of the enamine intermediate followed by 1,5-exo-dig cyclization. 5-Amino-1H-pyrrolo-3-carboxylates react with 1,3-diketones, affording pyrrolo[1,2-a]pyrimidine-7-carboxylates, and are easily converted into 2-diazo-2H-pyrrole-4-carboxylates. These compounds demonstrate the reactivity of both diazo compounds, giving pyrrole-containing products of intra/intermolecular azo coupling, and carbenes to give pyrrole-containing insertion products into CH and OH bonds under photolysis.
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Total citations:
41
Citations from 2024:
6
(14%)
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GOST
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Galenko E. E. et al. Isoxazole strategy for the synthesis of α-aminopyrrole derivatives // Journal of Organic Chemistry. 2019. Vol. 84. No. 17. pp. 11275-11285.
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Galenko E. E., Linnik S. A., Khoroshilova O. V., Novikov M. S., Khlebnikov A. F. Isoxazole strategy for the synthesis of α-aminopyrrole derivatives // Journal of Organic Chemistry. 2019. Vol. 84. No. 17. pp. 11275-11285.
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TY - JOUR
DO - 10.1021/acs.joc.9b01634
UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b01634
TI - Isoxazole strategy for the synthesis of α-aminopyrrole derivatives
T2 - Journal of Organic Chemistry
AU - Galenko, Ekaterina E
AU - Linnik, Stanislav A
AU - Khoroshilova, Olesya V
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2019
DA - 2019/08/06
PB - American Chemical Society (ACS)
SP - 11275-11285
IS - 17
VL - 84
PMID - 31385507
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2019_Galenko,
author = {Ekaterina E Galenko and Stanislav A Linnik and Olesya V Khoroshilova and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {Isoxazole strategy for the synthesis of α-aminopyrrole derivatives},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b01634},
number = {17},
pages = {11275--11285},
doi = {10.1021/acs.joc.9b01634}
}
Cite this
MLA
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Galenko, Ekaterina E., et al. “Isoxazole strategy for the synthesis of α-aminopyrrole derivatives.” Journal of Organic Chemistry, vol. 84, no. 17, Aug. 2019, pp. 11275-11285. https://pubs.acs.org/doi/10.1021/acs.joc.9b01634.