1,3-二氢-3-亚烷基-吲哚-2-酮的膦催化合成研究

doi:10.6023/cjoc202201030

摘要/Abstract

报道了一类三(4-甲氧基苯基)膦催化联烯酰亚胺与吲哚-2-酮之间的迈克尔加成/双键移位串联反应. 该反应条件温和, 操作简单, 产物收率较高, 具有较好的底物适应性和化学选择性, 为1,3-二氢-3-亚烷基-吲哚-2-酮骨架的构建提供了一种有效的新方法, 最后, 还提出了可能的反应历程.

关键词: 吲哚-2-酮, 联烯, 膦催化, 迈克尔加成反应, 双键移位

A P(4-OMe-C₆H₄)₃-catalyzed Michael addition/double bond migration tandem reaction between allenyl imide and indol-2-ones was developed. This synthetic strategy for diverse 1,3-dihydro-3-alkylidene-2H-indol-2-ones features operationally simple, good substrate scope, high chemoselectivity and mild reaction conditions. The proposed reaction mechanism is also provided.

Key words: indol-2-one, allene, phosphine catalysis, Michael addition, double bond migration

引用此文

李婧婕, 王宇豪, 孟甜甜, 黄毅勇. 1,3-二氢-3-亚烷基-吲哚-2-酮的膦催化合成研究[J]. 有机化学, 2022, 42(7): 2222-2228.

Jingjie Li, Yuhao Wang, Tiantian Meng, Yiyong Huang. Phosphine-Catalyzed Synthesis of 1,3-Dihydro-3-alkylidene-2H-indol-2-ones[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2222-2228.

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图/表 6

图1. 含1,3-二氢-3-亚烷基-吲哚-2-酮骨架的天然产物和药物分子

Figure 1. Representative natural products and pharmaceuticals containing 1,3-dihydro-3-alkylidene-2H-indol-2-one core structure

图式1. 1,3-二氢-3-亚烷基-吲哚-2-酮类化合物的合成策略

Scheme 1. Synthetic strategies for 1,3-dihydro-3-alkylidene-2H- indol-2-ones

Entry	Catalyst	Solvent	Time/h	Yield^b/%
Entry	Catalyst	Solvent	Time/h	3a	4a
1	PBu₃	EtOAc	48	34^c	34^c
2	PBu₃	Et₂O	48	49	—
3	P(4-MeOC₆H₄)₃	Et₂O	18	62	—
4	P(4-MeOC₆H₄)₃	THF	48	38	39
5	P(4-MeOC₆H₄)₃	DCE	48	42	36
6	P(4-MeOC₆H₄)₃	MTBE	48	10	35
7	P(4-MeOC₆H₄)₃	CH₃CN	48	50	—
8	P(4-MeOC₆H₄)₃	CH₃OH	48	—	—
9	P(4-MeOC₆H₄)₃	DMF	48	72	—
10	P(4-MeOC₆H₄)₃	DMF	24	81^d	—

表1. 反应条件优化a

Table 1. Optimization of the reaction conditions

表2. 吲哚-2-酮的底物适应性a

Table 2. Substrate scope of indol-2-one

图2. (Z)-3a的X射线单晶结构图

Figure 2. X-Ray crystal structure of (Z)-3a

图式2. 可能的反应机理

Scheme 2. Proposed reaction mechanism

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