Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow
Publication type: Journal Article
Publication date: 2018-11-27
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30479132
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A general strategy for the synthesis of 3,4-dioxygenated quinolin-2-one natural products is reported. The key step is a regioselective insertion of arynes into unsymmetric imides. When performed in continuous flow, the reaction proceeds within minutes, while lower yields and longer reaction times are observed in batch. The resulting N-acylated 2-aminobenzophenones were transformed to (±)-peniprequinolone, (±)-aflaquinolones E and F, (±)-6-deoxyaflaquinolone E, (±)-quinolinones A and B, and (±)-aniduquinolone C in 1-3 steps.
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Total citations:
28
Citations from 2025:
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(10.71%)
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GOST
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Schwan J. et al. Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow // Organic Letters. 2018. Vol. 20. No. 23. pp. 7661-7664.
GOST all authors (up to 50)
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Schwan J., Kleoff M., Hartmayer B., Heretsch P., Christmann M. Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow // Organic Letters. 2018. Vol. 20. No. 23. pp. 7661-7664.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b03392
UR - https://doi.org/10.1021/acs.orglett.8b03392
TI - Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow
T2 - Organic Letters
AU - Schwan, Johannes
AU - Kleoff, Merlin
AU - Hartmayer, Bence
AU - Heretsch, Philipp
AU - Christmann, Mathias
PY - 2018
DA - 2018/11/27
PB - American Chemical Society (ACS)
SP - 7661-7664
IS - 23
VL - 20
PMID - 30479132
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Schwan,
author = {Johannes Schwan and Merlin Kleoff and Bence Hartmayer and Philipp Heretsch and Mathias Christmann},
title = {Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.orglett.8b03392},
number = {23},
pages = {7661--7664},
doi = {10.1021/acs.orglett.8b03392}
}
Cite this
MLA
Copy
Schwan, Johannes, et al. “Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow.” Organic Letters, vol. 20, no. 23, Nov. 2018, pp. 7661-7664. https://doi.org/10.1021/acs.orglett.8b03392.