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

doi:10.6023/cjoc202010023

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1691-1702.DOI: 10.6023/cjoc202010023 Previous Articles Next Articles

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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^a, 姜风轩^b, 程凯^b^,^*(), 黄乐浩^a^,^*()

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 发布日期:2020-12-05
通讯作者: 程凯, 黄乐浩
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)

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

Honglei Jin^a, Fengxuan Jiang^b, Kai Cheng^b^,^*(), Lehao Huang^a^,^*()

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

Received:2020-10-16 Revised:2020-11-11 Published:2020-12-05
Contact: Kai Cheng, Lehao Huang
About author:
* Corresponding authors. E-mail: chengkai@usx.edu.cn;
E-mail: rjhlh@wmu.edu.cn.
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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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

Cite this article

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.

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Fig. & Tab. 9

References 20

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Entry	Catalyst/mol%	Additive	Solvent	Yield^b/%
1	Pd(OAc)₂	KOAc	1,4-Dioxane	61
2	Pd(OAc)₂	PhCOOK	1,4-Dioxane	68
3	Pd(OAc)₂	PhCOOK	DMF	N.D.
4	Pd(OAc)₂	PhCOOK	Xylene	82
5	Pd(OAc)₂	PhCOOK	DMSO	N.D.
6	Pd(OAc)₂	PhCOOK	t-BuOH	75
7	Pd(OAc)₂	PhCOOK	DCE	86
8	Pd(OAc)₂	—	DCE	Trace
9	Pd(OAc)₂	AgOAc	DCE	Trace
10	Pd(OAc)₂	NaOAc	DCE	49
11	Pd(OAc)₂	K₂CO₃	DCE	45
12	Pd(OAc)₂	Cs₂CO₃	DCE	Trace
13	Pd(OAc)₂	HOAc	DCE	18
14	Pd(OAc)₂	CF₃COOH	DCE	N.D.
15	PdCl₂	PhCOOK	DCE	83
16	Pd(PPh₃)₄	PhCOOK	DCE	36
17	Pd₂(dba)₃	PhCOOK	DCE	30
18	Pd(CH₃CN)₂Cl₂	PhCOOK	DCE	80

Entry	Catalyst/mol%	Additive	Solvent	Yield^b/%
1	Pd(OAc)₂	KOAc	1,4-Dioxane	61
2	Pd(OAc)₂	PhCOOK	1,4-Dioxane	68
3	Pd(OAc)₂	PhCOOK	DMF	N.D.
4	Pd(OAc)₂	PhCOOK	Xylene	82
5	Pd(OAc)₂	PhCOOK	DMSO	N.D.
6	Pd(OAc)₂	PhCOOK	t-BuOH	75
7	Pd(OAc)₂	PhCOOK	DCE	86
8	Pd(OAc)₂	—	DCE	Trace
9	Pd(OAc)₂	AgOAc	DCE	Trace
10	Pd(OAc)₂	NaOAc	DCE	49
11	Pd(OAc)₂	K₂CO₃	DCE	45
12	Pd(OAc)₂	Cs₂CO₃	DCE	Trace
13	Pd(OAc)₂	HOAc	DCE	18
14	Pd(OAc)₂	CF₃COOH	DCE	N.D.
15	PdCl₂	PhCOOK	DCE	83
16	Pd(PPh₃)₄	PhCOOK	DCE	36
17	Pd₂(dba)₃	PhCOOK	DCE	30
18	Pd(CH₃CN)₂Cl₂	PhCOOK	DCE	80

Entry	Product	Yield^b/%
1	3a	86 (76^c)
2	3b	66
3	3c	72
4	3d	62
5^d	3d	61
6^e	3e	78
7^e	3e	80

Entry	Product	Yield^b/%
1	3a	86 (76^c)
2	3b	66
3	3c	72
4	3d	62
5^d	3d	61
6^e	3e	78
7^e	3e	80

Entry	Product	Yield^b/%	Entry	Product	Yield^b/%
1	3f	82 (74^c)	6	3k	70
2	3g	79	7	3l	78
3	3h	64	8	3m	71
4	3i	55	9	3n	52
5	3j	76	10^d	3o	56

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

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

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