Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines
Тип публикации: Journal Article
Дата публикации: 2017-08-03
scimago Q2
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БС2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Краткое описание
A convenient gram-scale method for the preparation of 2-halo-2H-azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh2(Piv)4, while FeCl2·4H2O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.
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Rostovskii N. V. et al. Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines // Synthesis. 2017. Vol. 49. No. 19. pp. 4478-4488.
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Rostovskii N. V., Agafonova A. V., Smetanin I. A., Novikov M. S., Khlebnikov A. F., Ruvinskaya J. O., Starova G. L. Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines // Synthesis. 2017. Vol. 49. No. 19. pp. 4478-4488.
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TY - JOUR
DO - 10.1055/s-0036-1590822
UR - https://doi.org/10.1055/s-0036-1590822
TI - Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines
T2 - Synthesis
AU - Rostovskii, Nikolai V
AU - Agafonova, Anastasiya V
AU - Smetanin, Ilia A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Ruvinskaya, Julia O
AU - Starova, G. L.
PY - 2017
DA - 2017/08/03
PB - Georg Thieme Verlag KG
SP - 4478-4488
IS - 19
VL - 49
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2017_Rostovskii,
author = {Nikolai V Rostovskii and Anastasiya V Agafonova and Ilia A Smetanin and Mikhail S. Novikov and Alexander F Khlebnikov and Julia O Ruvinskaya and G. L. Starova},
title = {Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines},
journal = {Synthesis},
year = {2017},
volume = {49},
publisher = {Georg Thieme Verlag KG},
month = {aug},
url = {https://doi.org/10.1055/s-0036-1590822},
number = {19},
pages = {4478--4488},
doi = {10.1055/s-0036-1590822}
}
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MLA
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Rostovskii, Nikolai V., et al. “Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines.” Synthesis, vol. 49, no. 19, Aug. 2017, pp. 4478-4488. https://doi.org/10.1055/s-0036-1590822.
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