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Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
Тип публикации: Journal Article
Дата публикации: 2022-09-02
PubMed ID:
36080448
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Краткое описание
A method for the [2+3] pyrroline annulation to the six-membered non-aromatic enols using 3-aryl-2H-azirines as annulation agents is developed in the current study. The reaction proceeds as a formal (3+2) cycloaddition via the N1-C2 azirine bond cleavage and is catalyzed by both Cu(II) and Cu(I) compounds. The new annulation method can be applied to prepare pyrrolo[3,2-c]quinoline, chromeno[3,4-b]pyrrole, and naphtho[1,8-ef]indole derivatives in good to excellent yields from enols of the quinolin-2-one, 2H-chromen-2-one, and 1H-phenalen-1-one series.
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Sakharov P. A. et al. Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds // Molecules. 2022. Vol. 27. No. 17. p. 5681.
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Sakharov P. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds // Molecules. 2022. Vol. 27. No. 17. p. 5681.
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TY - JOUR
DO - 10.3390/molecules27175681
UR - https://www.mdpi.com/1420-3049/27/17/5681
TI - Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
T2 - Molecules
AU - Sakharov, Pavel A
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2022
DA - 2022/09/02
PB - MDPI
SP - 5681
IS - 17
VL - 27
PMID - 36080448
SN - 1420-3049
ER -
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@article{2022_Sakharov,
author = {Pavel A Sakharov and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {MDPI},
month = {sep},
url = {https://www.mdpi.com/1420-3049/27/17/5681},
number = {17},
pages = {5681},
doi = {10.3390/molecules27175681}
}
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Sakharov, Pavel A., et al. “Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds.” Molecules, vol. 27, no. 17, Sep. 2022, p. 5681. https://www.mdpi.com/1420-3049/27/17/5681.