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.
使用9-氮杂环庚三烯（9-AJ）催化的β,γ-二酰基-α-炔酰基苯胺衍生物的串联酰基转移-区域选择性环化反应，成功实现了吡咯基4-喹啉酮生物碱喹诺内酯及其类似物的合成。此外，这种有机催化反应已成功用于以中等到良好的产率合成多种3-酰基-4-喹啉酮。包括时间进程核磁共振（NMR）实验在内的机理研究表明，9-AJ向炔酮体系的1,4-加成可被视为该喹啉酮合成中的速率决定步骤。
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