Chinese Journal of Organic Chemistry >
Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids
Received date: 2020-10-16
Revised date: 2020-11-11
Online published: 2020-12-05
Supported by
Zhejiang Provincial Natural Science Foundation of China(LY18B020010); Opening Project of the Zhejiang Provincial Top Key Discipline of Pharmaceutical Sciences(201705); Foundation of Wenzhou Medical University Renji College(RJRC14001)
A practical methodology for the palladium-catalyzed regioselective alkylation of 8-C—H bonds in 1-naphthyl- amides containing a quinolinamide moiety as bidentate directing group with functionalized alkyl halides is reported. Various functionalized alkyl halides includingα-bromo esters and ketones can be employed as coupling partners, providing exclusively 8-alkyl-1-naphthylamine derivatives. In particular, the alkylated products with these ester and carbonyl groups can readily be further converted into the core structures of aporphine and aristolactam alkaloids respectively.
Honglei Jin , Fengxuan Jiang , Kai Cheng , Lehao Huang . Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1691 -1702 . DOI: 10.6023/cjoc202010023
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