无金属催化炔酰胺分子内[4+2]环化反应合成四氢吲哚衍生物

doi:10.6023/cjoc202201006

有机化学 ›› 2022, Vol. 42 ›› Issue (5): 1501-1508.DOI: 10.6023/cjoc202201006 上一篇下一篇

研究论文

无金属催化炔酰胺分子内[4+2]环化反应合成四氢吲哚衍生物

张智鑫^a, 翟彤仪^a, 朱伯汉^b, 钱鹏程^b^,^*(), 叶龙武^a^,^c^,^*()

a 厦门大学化学化工学院福建厦门 361005
b 温州大学化学和材料工程学院浙江温州 325035
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2022-01-05 修回日期:2022-01-24 发布日期:2022-01-27
通讯作者: 钱鹏程, 叶龙武
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21772161)

Synthesis of Tetrahydroindole Derivatives via Metal-Free Intramolecular [4+2] Annulation of Ynamides

Zhixin Zhang^a, Tongyi Zhai^a, Bohan Zhu^b, Pengcheng Qian^b(), Longwu Ye^a^,^c()

a College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005
b College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-01-05 Revised:2022-01-24 Published:2022-01-27
Contact: Pengcheng Qian, Longwu Ye
About author:
^†These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(21772161)

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摘要/Abstract

报道了无金属催化4-硅氧基-3,5-二烯炔酰胺的分子内[4+2]环化反应合成四氢吲哚衍生物的方法. 在催化量三乙胺存在下, 通过炔酰胺与硅氧基二烯的分子内Diels-Alder反应, 可方便得到六元环环化产物. 该反应条件温和、无需过渡金属催化剂、底物普适性广, 为含有4-羟基氢化吲哚骨架的天然产物和活性分子的合成提供了一条简洁和高效的途径.

关键词: 环化反应, 无金属催化, 炔酰胺, 杂环合成

A metal-free reaction of 4-siloxy-3,5-diene ynamides via an intramolecular [4+2] annulation has been developed. In the presence of catalytic Et₃N, this protocol leads to the facile formation of six-membered cycloadducts. This reaction can proceed smoothly under mild condition without transition-metal-catalysts and its substrate scope is wide. This strategy provides a concise and practical protocol to synthesize natural product and bioactive compounds containing 4-hydroxyl hydroindole skeletons.

Key words: annulation reaction, metal-free catalysis, ynamides, heterocycle synthesis

引用此文

张智鑫, 翟彤仪, 朱伯汉, 钱鹏程, 叶龙武. 无金属催化炔酰胺分子内[4+2]环化反应合成四氢吲哚衍生物[J]. 有机化学, 2022, 42(5): 1501-1508.

Zhixin Zhang, Tongyi Zhai, Bohan Zhu, Pengcheng Qian, Longwu Ye. Synthesis of Tetrahydroindole Derivatives via Metal-Free Intramolecular [4+2] Annulation of Ynamides[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1501-1508.

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图/表 6

图1. 具有生物活性的4-羟基氢化吲哚衍生物

Figure 1. 4-Hydroxyhydrogenated indole derivatives with biological activity

Entry	Catalyst	Conditions	Yield^b/%
Entry	Catalyst	Conditions	2a	2aa
1	—	DCE, 80 ℃, 12 h	<5	<5
2	Cu(CH₃CN)₄PF₆	DCE, r.t., 2 h	<5	20
3	Cu(OTf)₂	DCE, r.t., 2 h	<5	15
4	MsOH	DCE, r.t., 0.5 h	<5	22
5	HNTf₂	DCE, r.t., 0.5 h	<5	<5
6^c	TFA	DCE, 80 ℃, 12 h	<5	<5
7	TfOH	DCE, r.t., 0.5 h	<5	<5
8^c	Et₃N	DCE, r.t., 24 h	<5	<1
9	Et₃N	DCE, 80 ℃, 12 h	99	<1
10	Pyrrolidine	DCE, 80 ℃, 12 h	99	<1

表1. 化合物2a的合成反应条件优化a

Table 1. Reaction conditions optimization for the synthesis of compound 2a

Entry	Yield/%	Entry	Yield/%
1	99	8	88
2	94	9	97
3	94	10	99
4	84	11	88 (1.2∶1 dr)
5	88	12	89
6	72	13	99
7	86

表2. 底物范围考察a

Table 2. Substrate scope investigation

图2. 2g的X单晶衍射

Figure 2. X-ray single crystal diffraction of 2g

图式1. 克量级反应和产物的进一步衍生化

Scheme 1. Gram-scale reaction and product elaboration

图式2. 机理研究

Scheme 2. Mechanistic studies

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无金属催化炔酰胺分子内[4+2]环化反应合成四氢吲哚衍生物

Synthesis of Tetrahydroindole Derivatives via Metal-Free Intramolecular [4+2] Annulation of Ynamides

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