Organic Letters, volume 21, issue 10, pages 3615-3619

2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives

Publication typeJournal Article
Publication date2019-05-07
Journal: Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.2
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A method of furo-annulation of 4-hydroxy-2-oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3-dihydrofuro[3,2- c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N-C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2 H-azirines for furo-annulation.

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GOST Copy
Sakharov P. A. et al. 2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives // Organic Letters. 2019. Vol. 21. No. 10. pp. 3615-3619.
GOST all authors (up to 50) Copy
Sakharov P. A., Rostovskii N. V., Khlebnikov A. F., Panikorovskii T. L., Novikov M. S. 2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives // Organic Letters. 2019. Vol. 21. No. 10. pp. 3615-3619.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.9b01043
UR - https://doi.org/10.1021%2Facs.orglett.9b01043
TI - 2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives
T2 - Organic Letters
AU - Sakharov, Pavel A
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Panikorovskii, T. L.
AU - Novikov, Mikhail S.
PY - 2019
DA - 2019/05/07 00:00:00
PB - American Chemical Society (ACS)
SP - 3615-3619
IS - 10
VL - 21
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
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BibTex Copy
@article{2019_Sakharov
author = {Pavel A Sakharov and Nikolai V Rostovskii and Alexander F Khlebnikov and T. L. Panikorovskii and Mikhail S. Novikov},
title = {2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021%2Facs.orglett.9b01043},
number = {10},
pages = {3615--3619},
doi = {10.1021/acs.orglett.9b01043}
}
MLA
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MLA Copy
Sakharov, Pavel A., et al. “2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives.” Organic Letters, vol. 21, no. 10, May. 2019, pp. 3615-3619. https://doi.org/10.1021%2Facs.orglett.9b01043.
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