Iodine-Catalyzed Intramolecular Cyclization for the Synthesis of 2-Hydroxy-indolin-3-ones

doi:10.6023/cjoc202510019

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 961-967.DOI: 10.6023/cjoc202510019 Previous Articles Next Articles

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碘催化分子内环化2-羟基-吲哚-3-酮类化合物的合成

何雨蒙^a^,^†, 周风院^a^,^†, 江楠^a, 张玉琦^a, 王记江^a, 马豪杰^a^,^b^,^*()

^a 延安大学化学与化工学院陕西省化学反应工程重点实验室陕西省化学反应工程重点实验室陕西延安 716000
^b 山东协和学院医学院济南 250109

收稿日期:2025-10-23 修回日期:2025-11-21 发布日期:2025-12-25
通讯作者: 马豪杰
基金资助:
陕西省自然科学基础研究计划(2025JC-YBQN-129); 陕西省大学生创新创业训练计划(S202410719082); 山东省自然科学基金(ZR2025QC95)

Iodine-Catalyzed Intramolecular Cyclization for the Synthesis of 2-Hydroxy-indolin-3-ones

Yumeng He^a, Fengyuan Zhou^a, Nan Jiang^a, Yuqi Zhang^a, Jijiang Wang^a, Haojie Ma^a^,^b^,^*()

^a Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000
^b Medical College, Shandong Xiehe University, Jinan 250109

Received:2025-10-23 Revised:2025-11-21 Published:2025-12-25
Contact: Haojie Ma
About author:
†The authors contributed equally to this work.
†共同第一作者
Supported by:
Natural Science Foundation Research Project of Shaanxi Province(2025JC-YBQN-129); College Students’ Innovation and Entrepreneurship Training Program of Shaanxi Province(S202410719082); Natural Science Foundation Research Project of Shandong Province(ZR2025QC95)

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Abstract

A novel and efficient strategy for the synthesis of 2-hydroxy-indolin-3-ones through iodine-catalyzed intra- molecular cyclization of N-(2-acetylphenyl)picolinamide has been developed. This protocol features atom economy, metal-free, easy operation with cheap reagents, providing a useful and attractive route for the synthesis of 2-hydroxy- indolin-3-ones, which is widely presented in pharmaceuticals, biologically active molecules and natural products.

Key words: iodine, 2-hydroxy-indolin-3-ones, N-(2-acetylphenyl)picolinamide, intramolecular cyclization, metal-free

Cite this article

Yumeng He, Fengyuan Zhou, Nan Jiang, Yuqi Zhang, Jijiang Wang, Haojie Ma. Iodine-Catalyzed Intramolecular Cyclization for the Synthesis of 2-Hydroxy-indolin-3-ones[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 961-967.

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References 16

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Entry	Solvent	I₂/equiv.	Temp./℃	Yield^b/%
1	DMSO	0.5	100	37
2	Toluene	0.5	100	nd
3	MeCN	0.5	100	nd
4	DMSO	1.0	100	25
5	DMSO	0.6	100	32
6	DMSO	0.4	100	53
7	DMSO	0.3	100	33
8	DMSO	0.1	100	30
9^c	DMSO	0.4	100	nd
10^d	DMSO	0.4	100	40
11	DMSO	0.4	140	Trace
12	DMSO	0.4	120	56
13	DMSO	0.4	80	39
14	DMSO/H₂O (V/V=3/1)	0.4	120	69
15	DMSO/H₂O (V/V=2/1)	0.4	120	25
16	DMSO/H₂O (V/V=1/1)	0.4	120	Trace

Entry	Solvent	I₂/equiv.	Temp./℃	Yield^b/%
1	DMSO	0.5	100	37
2	Toluene	0.5	100	nd
3	MeCN	0.5	100	nd
4	DMSO	1.0	100	25
5	DMSO	0.6	100	32
6	DMSO	0.4	100	53
7	DMSO	0.3	100	33
8	DMSO	0.1	100	30
9^c	DMSO	0.4	100	nd
10^d	DMSO	0.4	100	40
11	DMSO	0.4	140	Trace
12	DMSO	0.4	120	56
13	DMSO	0.4	80	39
14	DMSO/H₂O (V/V=3/1)	0.4	120	69
15	DMSO/H₂O (V/V=2/1)	0.4	120	25
16	DMSO/H₂O (V/V=1/1)	0.4	120	Trace

碘催化分子内环化2-羟基-吲哚-3-酮类化合物的合成

Iodine-Catalyzed Intramolecular Cyclization for the Synthesis of 2-Hydroxy-indolin-3-ones

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