2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives
Pavel A Sakharov
1
,
T. L. Panikorovskii
1, 2
,
Publication type: Journal Article
Publication date: 2019-05-07
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31063384
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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27
Total citations:
27
Citations from 2024:
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(22%)
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GOST
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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)
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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.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.9b01043
UR - https://pubs.acs.org/doi/10.1021/acs.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
PB - American Chemical Society (ACS)
SP - 3615-3619
IS - 10
VL - 21
PMID - 31063384
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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://pubs.acs.org/doi/10.1021/acs.orglett.9b01043},
number = {10},
pages = {3615--3619},
doi = {10.1021/acs.orglett.9b01043}
}
Cite this
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://pubs.acs.org/doi/10.1021/acs.orglett.9b01043.