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Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles
Publication type: Journal Article
Publication date: 2021-03-26
PubMed ID:
33810476
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The latter were prepared by Rh2(oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-H-shift.
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7
Total citations:
7
Citations from 2024:
5
(71%)
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Zanakhov T. O. et al. Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles // Molecules. 2021. Vol. 26. No. 7. p. 1881.
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Zanakhov T. O., Galenko E. E., Kryukova M. A., Novikov M. S., Khlebnikov A. A. Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles // Molecules. 2021. Vol. 26. No. 7. p. 1881.
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TY - JOUR
DO - 10.3390/molecules26071881
UR - https://doi.org/10.3390/molecules26071881
TI - Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles
T2 - Molecules
AU - Zanakhov, Timur O
AU - Galenko, Ekaterina E
AU - Kryukova, Mariya A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander A
PY - 2021
DA - 2021/03/26
PB - MDPI
SP - 1881
IS - 7
VL - 26
PMID - 33810476
SN - 1420-3049
ER -
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BibTex (up to 50 authors)
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@article{2021_Zanakhov,
author = {Timur O Zanakhov and Ekaterina E Galenko and Mariya A Kryukova and Mikhail S. Novikov and Alexander A Khlebnikov},
title = {Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {MDPI},
month = {mar},
url = {https://doi.org/10.3390/molecules26071881},
number = {7},
pages = {1881},
doi = {10.3390/molecules26071881}
}
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MLA
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Zanakhov, Timur O., et al. “Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles.” Molecules, vol. 26, no. 7, Mar. 2021, p. 1881. https://doi.org/10.3390/molecules26071881.