通过9-AJ催化的α-炔丙酰苯胺衍生物的串联酰基转移-环化反应简便合成吡咯基4-喹啉酮生物碱喹喏拉克酸

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

作者信息

Saito Koya, Yoshida Masahito, Uekusa Hidehiro, Doi Takayuki

机构信息

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.

Department of Chemistry, School of Science, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8551, Japan.

出版信息

ACS Omega. 2017 Aug 9;2(8):4370-4381. doi: 10.1021/acsomega.7b00793. eCollection 2017 Aug 31.

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 ,-diacyl--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.