Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement
Nikolai Yu Tiuftiakov
1
,
Julia O Strelnikova
1
,
Ilya Filippov
1
,
Ilya P Filippov
1
,
Adel R Khaidarov
1
,
Publication type: Journal Article
Publication date: 2021-08-23
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34424720
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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Metrics
18
Total citations:
18
Citations from 2024:
9
(50%)
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GOST
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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)
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Tiuftiakov N. Yu., Strelnikova J. O., Filippov I., Filippov I. P., 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.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.1c02706
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.1c02706
TI - Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement
T2 - Organic Letters
AU - Tiuftiakov, Nikolai Yu
AU - Strelnikova, Julia O
AU - Filippov, Ilya
AU - Filippov, Ilya P
AU - Khaidarov, Adel R
AU - Khlebnikov, Alexander F
AU - Bunev, Alexander S.
AU - Novikov, Mikhail S.
AU - Rostovskii, Nikolai V
PY - 2021
DA - 2021/08/23
PB - American Chemical Society (ACS)
SP - 6998-7002
IS - 17
VL - 23
PMID - 34424720
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Tiuftiakov,
author = {Nikolai Yu Tiuftiakov and Julia O Strelnikova and Ilya Filippov and Ilya P Filippov and Adel R Khaidarov and Alexander F Khlebnikov and Alexander S. Bunev and Mikhail S. Novikov and Nikolai V Rostovskii},
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://pubs.acs.org/doi/10.1021/acs.orglett.1c02706},
number = {17},
pages = {6998--7002},
doi = {10.1021/acs.orglett.1c02706}
}
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://pubs.acs.org/doi/10.1021/acs.orglett.1c02706.