Organophosphoric Acid Catalyzed [3＋3] Cyclization for the Synthesis of Indenoquinolinedione Derivatives

doi:10.6023/cjoc202405040

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (12): 3727-3738.DOI: 10.6023/cjoc202405040 Previous Articles Next Articles

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有机磷酸催化的[3＋3]环化反应合成茚并喹啉二酮衍生物

郭昕彦^a^,^†, 于浩磊^a^,^†, 万洪林^a^,^†, 陆钰^a, 谭伟^a^,^*(), 石枫^a^,^b^,^*()

a 江苏师范大学化学与材料科学学院江苏徐州 221116
b 常州大学石油化工学院江苏常州 213164

收稿日期:2024-05-28 修回日期:2024-07-30 发布日期:2024-08-30
作者简介:
†共同第一作者.
基金资助:
国家自然科学基金(22125104); 国家自然科学基金(22301112); 江苏省自然科学基金(BK20210916); 本科生创新项目(202410320104Y); 本科生创新项目(XSJCX14139); 江苏省优秀科技创新团队资助项目.

Organophosphoric Acid Catalyzed [3＋3] Cyclization for the Synthesis of Indenoquinolinedione Derivatives

Xinyan Guo^a^,^†, Haolei Yu^a^,^†, Honglin Wan^a^,^†, Yu Lu^a, Wei Tan^a^,^*(), Feng Shi^a^,^b^,^*()

a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
b School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164

Received:2024-05-28 Revised:2024-07-30 Published:2024-08-30
Contact: *E-mail:fshi@jsnu.edu.cn;fshi@cczu.edu.cn;wtan@jsnu.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22125104); National Natural Science Foundation of China(22301112); Natural Science Foundation of Jiangsu Province(BK20210916); Undergraduate Students Innovative Project(202410320104Y); Undergraduate Students Innovative Project(XSJCX14139); Project for Excellent Scientific and Technological Innovation Team of Jiangsu Province.

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Abstract

An organophosphoric acid catalyzed [3＋3] cyclization of 2-arylidene-indan-1,3-diones with enaminones has been established, which afforded a series of structurally diverse indenoquinolinedione derivatives in moderate to excellent yields. This [3＋3] cyclization has some advantages such as mild reaction conditions, readily available catalyst and wide substrate range. This work not only provides an efficient method for constructing biologically important 1,4-dihydropyridine motif, but also suggests a possible reaction pathway and activation mode, therefore enriching the research contents of organophosphoric acid catalysis and [3＋3] cyclization reactions.

Key words: organophosphoric acid, [3＋3] cyclization, organocatalysis, enaminone, 1,4-dihydropyridine

Cite this article

Xinyan Guo, Haolei Yu, Honglin Wan, Yu Lu, Wei Tan, Feng Shi. Organophosphoric Acid Catalyzed [3＋3] Cyclization for the Synthesis of Indenoquinolinedione Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3727-3738.

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Fig. & Tab. 7

Figure 1. Representative bioactive molecules incorporating 1,4- dihydropyridine motif

Scheme 1. Profile of catalytic reactions for the synthesis of indenoquinolinedione derivatives

Entry	Cat.	Solvent	Yield^b/%
1	4a	Toluene	55
2	4a	EtOAc	59
3	4a	Acetone	90
4	4a	MeCN	77
5	4a	THF	71
6	4a	DCE	95
7	4b	DCE	89
8	4c	DCE	67
9	4d	DCE	84
10	4e	DCE	80
11	4f	DCE	14
12	4g	DCE	84
13	4h	DCE	75

Table 1. Optimization of reaction conditionsa

Table 2. Substrate scope of 2-arylidene-indan-1,3-diones 1a

Table 3. Substrate scope of enaminones 2a

Scheme 3. One-mmol-scale reaction and synthetic transformation

Scheme 4. Suggested reaction pathway

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有机磷酸催化的[3＋3]环化反应合成茚并喹啉二酮衍生物

Organophosphoric Acid Catalyzed [3＋3] Cyclization for the Synthesis of Indenoquinolinedione Derivatives

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Fig. & Tab. 7

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