Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives

Koya Saito; Masahito Yoshida; Hidehiro Uekusa; Takayuki Doi

doi:10.1021/acsomega.7b00793

Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives

Koya Saito, Masahito Yoshida, Hidehiro Uekusa, Takayuki Doi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4370-4381
Number of pages	12
Journal	ACS Omega
Volume	2
Issue number	8
DOIs	https://doi.org/10.1021/acsomega.7b00793
Publication status	Published - 2017 Aug 31

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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title = "Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives",

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.",

author = "Koya Saito and Masahito Yoshida and Hidehiro Uekusa and Takayuki Doi",

note = "Funding Information: Financial contribution from JSPS KAKENHI grant number JP15H05837 in Middle Molecular Strategy is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acsomega.7b00793",

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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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Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives

Abstract

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