TY - JOUR
T1 - Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives
AU - Saito, Koya
AU - Yoshida, Masahito
AU - Uekusa, Hidehiro
AU - Doi, Takayuki
N1 - Funding Information:
Financial contribution from JSPS KAKENHI grant number JP15H05837 in Middle Molecular Strategy is gratefully acknowledged.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/8/31
Y1 - 2017/8/31
N2 - 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.
AB - 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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U2 - 10.1021/acsomega.7b00793
DO - 10.1021/acsomega.7b00793
M3 - Article
AN - SCOPUS:85038848228
VL - 2
SP - 4370
EP - 4381
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 8
ER -