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

Koya Saito | Zendy; Masahito Yoshida | Zendy; Hidehiro Uekusa | Zendy; Takayuki Doi | Zendy

Open Access

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

Author(s) -

Koya Saito,

Masahito Yoshida,

Hidehiro Uekusa,

Takayuki Doi

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00793

Subject(s) - tandem , chemistry , catalysis , alkaloid , stereochemistry , combinatorial chemistry , organic chemistry , materials science , composite material

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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