Organic Letters, volume 22, issue 20, pages 7958-7963
Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters
Publication type: Journal Article
Publication date: 2020-10-07
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A method for the synthesis of densely substituted 4-pyrrolin-2-ones by Rh(II)-catalyzed denitrogenative transannulation of 1-alkyl-4-aryl-1H-1,2,3-triazoles with diazo esters has been developed. The reaction proceeds via an attack of the rhodium-bound carbene at the N2 atom of the triazole and the formation of unstable 3,4-dihydro-1,2,4-triazine, which further undergoes ring contraction to a 4-pyrrolin-2-one under rhodium catalysis. The method is inapplicable to 1,2,3-triazoles with primary alkyl substituent at C4, which afford stable 1,2,3-triazol-3-ium ylides as the main products.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Koronatov A. et al. Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters // Organic Letters. 2020. Vol. 22. No. 20. pp. 7958-7963.
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Koronatov A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters // Organic Letters. 2020. Vol. 22. No. 20. pp. 7958-7963.
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TY - JOUR
DO - 10.1021/acs.orglett.0c02893
UR - https://doi.org/10.1021%2Facs.orglett.0c02893
TI - Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters
T2 - Organic Letters
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
AU - Koronatov, Aleksandr
PY - 2020
DA - 2020/10/07 00:00:00
PB - American Chemical Society (ACS)
SP - 7958-7963
IS - 20
VL - 22
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2020_Koronatov,
author = {Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov and Aleksandr Koronatov},
title = {Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021%2Facs.orglett.0c02893},
number = {20},
pages = {7958--7963},
doi = {10.1021/acs.orglett.0c02893}
}
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Koronatov, Aleksandr, et al. “Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters.” Organic Letters, vol. 22, no. 20, Oct. 2020, pp. 7958-7963. https://doi.org/10.1021%2Facs.orglett.0c02893.