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Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
Publication type: Journal Article
Publication date: 2017-08-09
scimago Q1
wos Q2
SJR: 0.773
CiteScore: 7.1
Impact factor: 4.3
ISSN: 24701343
PubMed ID:
31457730
General Chemistry
General Chemical Engineering
Abstract
The synthesis of pyrrolyl 4-quinolinone alkaloid, quinolactacide, and its analogues was successfully achieved using 9-azajulolidine (9-AJ)-catalyzed tandem acyl transfer-regioselective cyclization of N,N-diacyl-o-alkynoylaniline derivatives. In addition, this organocatalytic reaction was successfully utilized for the synthesis of a variety of 3-acyl-4-quinolinones in moderate-to-good yields. Mechanistic studies, including a time course nuclear magnetic resonance (NMR) experiment, indicated that the 1,4-addition of 9-AJ to an ynone system can be considered to be the rate-determining step in this quinolinone synthesis.
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16
Total citations:
16
Citations from 2025:
1
(6.25%)
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GOST
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Saito K. et al. Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives // ACS Omega. 2017. Vol. 2. No. 8. pp. 4370-4381.
GOST all authors (up to 50)
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Saito K., Yoshida M., Uekusa H., Doi T. Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives // ACS Omega. 2017. Vol. 2. No. 8. pp. 4370-4381.
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RIS
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TY - JOUR
DO - 10.1021/acsomega.7b00793
UR - https://doi.org/10.1021/acsomega.7b00793
TI - Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
T2 - ACS Omega
AU - Saito, Koya
AU - Yoshida, Masahito
AU - Uekusa, Hidehiro
AU - Doi, Takayuki
PY - 2017
DA - 2017/08/09
PB - American Chemical Society (ACS)
SP - 4370-4381
IS - 8
VL - 2
PMID - 31457730
SN - 2470-1343
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Saito,
author = {Koya Saito and Masahito Yoshida and Hidehiro Uekusa and Takayuki Doi},
title = {Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives},
journal = {ACS Omega},
year = {2017},
volume = {2},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acsomega.7b00793},
number = {8},
pages = {4370--4381},
doi = {10.1021/acsomega.7b00793}
}
Cite this
MLA
Copy
Saito, Koya, et al. “Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives.” ACS Omega, vol. 2, no. 8, Aug. 2017, pp. 4370-4381. https://doi.org/10.1021/acsomega.7b00793.