Organic Letters, volume 23, issue 17, pages 6998-7002

Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement

Publication typeJournal Article
Publication date2021-08-23
Journal: Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.2
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A one-step synthesis of cytotoxic 2-aroylpyrimidines by the denitrogenative reaction of 1-tosyl-1,2,3-triazoles with isoxazoles under rhodium catalysis has been developed. According to the density functional theory calculations and control experiments, the disclosed reaction proceeds via the rearrangement of an oxadiazatetraene intermediate involving a cascade of intramolecular aza-Diels-Alder and retro-aza-Diels-Alder reactions. The presence of a substituent at C4 of the isoxazole is a prerequisite for the formation of the pyrimidines.

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GOST Copy
Tiuftiakov N. Yu. et al. Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement // Organic Letters. 2021. Vol. 23. No. 17. pp. 6998-7002.
GOST all authors (up to 50) Copy
Tiuftiakov N. Yu., Strelnikova J. O., Filippov I., Khaidarov A. R., Khlebnikov A. F., Bunev A. S., Novikov M. S., Rostovskii N. V. Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement // Organic Letters. 2021. Vol. 23. No. 17. pp. 6998-7002.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.1c02706
UR - https://doi.org/10.1021%2Facs.orglett.1c02706
TI - Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement
T2 - Organic Letters
AU - Strelnikova, Julia O
AU - Khlebnikov, Alexander F
AU - Bunev, Alexander S.
AU - Novikov, Mikhail S.
AU - Rostovskii, Nikolai V
AU - Tiuftiakov, Nikolai Yu
AU - Filippov, Ilya
AU - Khaidarov, Adel R
PY - 2021
DA - 2021/08/23 00:00:00
PB - American Chemical Society (ACS)
SP - 6998-7002
IS - 17
VL - 23
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
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BibTex Copy
@article{2021_Tiuftiakov
author = {Julia O Strelnikova and Alexander F Khlebnikov and Alexander S. Bunev and Mikhail S. Novikov and Nikolai V Rostovskii and Nikolai Yu Tiuftiakov and Ilya Filippov and Adel R Khaidarov},
title = {Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Facs.orglett.1c02706},
number = {17},
pages = {6998--7002},
doi = {10.1021/acs.orglett.1c02706}
}
MLA
Cite this
MLA Copy
Tiuftiakov, Nikolai Yu., et al. “Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement.” Organic Letters, vol. 23, no. 17, Aug. 2021, pp. 6998-7002. https://doi.org/10.1021%2Facs.orglett.1c02706.
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