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Molecules, volume 26, issue 7, pages 1881

Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles

Publication typeJournal Article
Publication date2021-03-26
Journal: Molecules
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor4.6
ISSN14203049
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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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
TY - JOUR
DO - 10.3390/molecules26071881
UR - https://doi.org/10.3390%2Fmolecules26071881
TI - Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles
T2 - Molecules
AU - Galenko, Ekaterina E
AU - Kryukova, Mariya A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander A
AU - Zanakhov, Timur O
PY - 2021
DA - 2021/03/26 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 1881
IS - 7
VL - 26
PMID - 33810476
SN - 1420-3049
ER -
BibTex |
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BibTex Copy
@article{2021_Zanakhov
author = {Ekaterina E Galenko and Mariya A Kryukova and Mikhail S. Novikov and Alexander A Khlebnikov and Timur O Zanakhov},
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 = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {mar},
url = {https://doi.org/10.3390%2Fmolecules26071881},
number = {7},
pages = {1881},
doi = {10.3390/molecules26071881}
}
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%2Fmolecules26071881.
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