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2021 , Vol. 41 >Issue 4: 1691 - 1702

DOI: https://doi.org/10.6023/cjoc202010023

研究论文

钯催化1-萘酰胺的8-烷基化反应及其在阿朴菲和马兜铃内酰胺类生物碱骨架合成中的应用

  • 金红蕾 ,
  • 姜风轩 ,
  • 程凯 ,
  • 黄乐浩
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  • a 温州医科大学药学院 浙江温州 325035
    b 绍兴文理学院化学化工学院 浙江省精细化学品传统工艺替代技术研究重点实验室 浙江绍兴 312000

收稿日期: 2020-10-16

  修回日期: 2020-11-11

  网络出版日期: 2020-12-05

基金资助

浙江省自然科学基金(LY18B020010); 浙江省药学重中之重一级学科开放基金(201705); 温州医科大学仁济学院启动基金(RJRC14001)

收起

Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids

  • Honglei Jin ,
  • Fengxuan Jiang ,
  • Kai Cheng ,
  • Lehao Huang
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  • a School of Pharmaceutical Science, Wenzhou Medical University, Wenzhou, Zhejiang 325035
    b Key Laboratory of Alternative Technologies for Fine Chemicals Process, College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000
* Corresponding authors. E-mail: ;
E-mail:

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)

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摘要

报道了一种钯催化1-萘酰胺的8位碳氢键烷基化反应. 在该反应中,喹啉甲酰胺作为N,N-双齿螯合基团, 各种取代的α-溴乙酸烷基酯以及α-溴代苯乙酮作为烷基化试剂, 高效、高区域选择性地合成了8-烷基-1-萘胺衍生物. 最后, 将含酯基和酮基的烷基化产物分别通过相应的衍生化反应合成具有多种生物活性的阿朴菲和马兜铃内酰胺类生物碱结构单元.

关键词： 钯催化; 烷基化; 1-萘酰胺; 阿朴菲类生物碱; 马兜铃内酰胺类生物碱

本文引用格式

金红蕾 , 姜风轩 , 程凯 , 黄乐浩 . 钯催化1-萘酰胺的8-烷基化反应及其在阿朴菲和马兜铃内酰胺类生物碱骨架合成中的应用[J]. 有机化学, 2021 , 41(4) : 1691 -1702 . DOI: 10.6023/cjoc202010023

Abstract

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.

Key words： palladium-catalyzed; alkylation; 1-naphthylamides; aporphine alkaloids; aristolactam alkaloids

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