Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion

doi:10.6023/cjoc202204019

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2867-2876.DOI: 10.6023/cjoc202204019 Previous Articles Next Articles

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可见光促进异腈插入反应合成硒代螺环[吲哚-3,3'-喹啉]衍生物

刘浩阳, 孙爽爽, 马献力^*(), 陈艳艳, 徐燕丽^*()

桂林医学院药学院广西桂林 541004

收稿日期:2022-04-07 修回日期:2022-05-27 发布日期:2022-06-08
通讯作者: 马献力, 徐燕丽
基金资助:
国家自然科学基金(21861015); 广西高等学校千名中青年骨干教师培育计划资助项目

Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion

Haoyang Liu, Shuangshuang Sun, Xianli Ma(), Yanyan Chen, Yanli Xu()

College of Pharmacy, Guilin Medical University, Guilin, Guangxi 541004

Received:2022-04-07 Revised:2022-05-27 Published:2022-06-08
Contact: Xianli Ma, Yanli Xu
Supported by:
National Natural Science Foundation of China(21861015); Cultivation Plan of Thousands of Young and Middle-aged Backbone Teachers in Guangxi Colleges and Universities

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Abstract

A photosensitizer-free visible-light-promoted isocyanide insertion protocol for the synthesis of selenylated spiro[indole-3,3'-quinoline] derivatives has been developed, which has the advantages of functional group tolerance, broad substrate scope, simple operation, and good yield. 2-Phenyl-2'-(phenylselanyl)-6'-(trifluoromethyl)-4'H-spiro[indole-3,3'-quinoline] (3g), 5-bromo-2'-((4-fluorophenyl)selanyl)-2-phenyl-4'H-spiro[indole-3,3'-quinoline] (4d) and 2-phenyl-2'-((4-(trifluoromethyl)phenyl)selanyl)-4'H-spiro[indole-3,3'-quinoline] (4g) showed potent cancer-cell-growth inhibitory activities by methyl thiazolyl tetrazolium (MTT) assay.

Key words: visible-light-promoted, isocyanides, spirocyclization, selenylated spiro[indole-3,3'-quinoline]

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Haoyang Liu, Shuangshuang Sun, Xianli Ma, Yanyan Chen, Yanli Xu. Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2867-2876.

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Fig. & Tab. 9

Figure 1. Spiroindolenine natural products

Scheme 1. Synthesis of selenylated spiroindolenine compounds

Entry	Oxidant	Solvent	Yield/%
1^b	—	MeCN	30
2^c	TBHP	MeCN	57
3	TBHP	MeCN	83
4^d	TBHP	MeCN	77
5	H₂O₂	MeCN	50
6	TBHP	DMSO	Trace
7	TBHP	THF	31
8	TBHP	EtOH	Trace
9^e	TBHP	MeCN	83
10^f	TBHP	MeCN	73
11^g	TBHP	MeCN	10
12^h	TBHP	MeCN	78

Table 1. Optimized conditionsa

Table 2. Substrate scope of isocyanidesa

Table 3. Substrate scope of diselenidesa

Scheme 2. Control experiments for selenylative spirocyclization of 1a

Scheme 3. Possible pathways for the formation of 3a

Figure 2. Anticancer activity of 3g, 4d and 4g

Scheme 4. Synthetic application of 3j to 5

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可见光促进异腈插入反应合成硒代螺环[吲哚-3,3'-喹啉]衍生物

Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion

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References 17

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