Facile Synthesis of Z/E-3-Arylmethylidene-2,3-dihydroindol-2-one under Solvent-Free Conditions

Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (10): 1414-1417. Previous Articles Next Articles

Reports

无溶剂条件下合成顺/反3-芳基亚甲基-2,3-二氢-吲哚-2-酮类化合物

徐天图，汪顺义，纪顺俊*

(苏州大学化学化工学院江苏省有机合成重点实验室苏州 215123)

收稿日期:2005-11-16 修回日期:2006-02-20 发布日期:2006-09-19
通讯作者: 纪顺俊

Facile Synthesis of Z/E-3-Arylmethylidene-2,3-dihydroindol-2-one under Solvent-Free Conditions

XU Tian-Tu,WANG Shun-Yi,JI Shun-Jun*

(Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineer-ing,
Suzhou University, Suzhou 215123)

Received:2005-11-16 Revised:2006-02-20 Published:2006-09-19
Contact: JI Shun-Jun

Abstract

A series of 3-arylmethylidene-2,3-dihydroindol-2-one derivatives 3 were conveniently synthesized by the condensation of aromatic aldehydes with 2-dihydroindol-2-one under basic and solvent-free conditions by grinding. All the products were determined by ¹H NMR, IR, and HRMS spectra, with the configurations of (Z)-3e and (Z)-3j confirmed by X-ray analysis.

Key words: 3-arylmethylidene-2,3-dihydroindol-2-one, 2-oxoindole, knoevenagel condensation, solvent-free

Cite this article

XU Tian-Tu,WANG Shun-Yi,JI Shun-Jun*. Facile Synthesis of Z/E-3-Arylmethylidene-2,3-dihydroindol-2-one under Solvent-Free Conditions[J]. Chin. J. Org. Chem., 2006, 26(10): 1414-1417.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[2]	Kun Zhou, Yangjie Mao, Fengwei Wu, Shaojie Lou, Danqian Xu. Recent Advances in C—H Bond Functionalization under Mechanochemical Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4623-4638.
[3]	Shi Dapeng, Duan Zhongyu. Propargylamine Synthesis via Three-Component Coupling Reaction Catalyzed by Recyclable Cu Nanoparticles under Solvent-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1316-1322.
[4]	Wang Lingfeng, Qian Ying. Near-Infrared Quinoline-Fluoroborodipyrrole Dye: Synthesis and Lysosomal Fluorescence Imaging [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1246-1250.
[5]	Ding Yuxin, Ma Yongmin, Chen Jing. Novel Three-Component Annulation for the Synthesis of 2,4,6-Triaryl-pyrimidines under Solvent-Free and Catalyst-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4357-4363.
[6]	Zhou Xiang, Zhou Fei, Jia Xiaoliang, Yu Jiawei, Shen Qi, Zhang Yunxiao, Shi Weimin. Solvent-Free Aldol Reaction of β-Porphyrin Formaldehyde with Ketone [J]. Chin. J. Org. Chem., 2019, 39(7): 2084-2088.
[7]	Yan Shiqiang, Guo Wei, Wang Wensheng, Zhang Wei. Zinc-Proline Complex Catalyzed Knoevenagel Condensation in Water [J]. Chin. J. Org. Chem., 2019, 39(5): 1469-1474.
[8]	Liu Jing, Wan Cong, Zheng Aili, Wang Lianyue, Yin Kaiyue, Liu Dandan, Wang Shengde, Ren Lanhui, Gao Shuang. α-Oxygenation of Benzylic Ethers to Esters Using MnO_x-N@C Catalyst [J]. Chin. J. Org. Chem., 2019, 39(3): 811-820.
[9]	Liu Tianbao, Peng Yanfen, Wang Yajie, Yong Jiayuan, Wang Xin. Synthesis of Thioamidoguanidine Derivatives under Solvent-Free Grinding Conditions [J]. Chin. J. Org. Chem., 2018, 38(4): 969-974.
[10]	Cai Liangzhen, Huang Zhen, Yang Liqun, Xie Xiaomin, Tao Xiaochun. Selective Aerobic Oxidation of Benzylic Alcohols Catalyzed by CuBr/1,8-Diazabicyclo[5.4.0]undec-7-ene [J]. Chin. J. Org. Chem., 2018, 38(12): 3326-3331.
[11]	Wang Xiang, Chen Ping, Zhi Sanjun, Hu Huayou, Kan Yuhe. CBr₄-Promoted Efficient Synthesis of 2-(1H-Benzo[d] imidazol-2-yl)-3-arylacrylonitriles [J]. Chin. J. Org. Chem., 2018, 38(11): 3123-3126.
[12]	Zhang Qingyang, Wang Xiaojian, Xiao Qiong, Yin Dali. One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI [J]. Chin. J. Org. Chem., 2017, 37(4): 954-958.
[13]	Xu Zhaohui, Zhou Peng, Liu Deyong. Efficient One-Pot Synthesis of 3,3-Dimethyl-diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5-dione-9-thione Derivatives [J]. Chin. J. Org. Chem., 2016, 36(5): 1099-1103.
[14]	Tan Nianyuan, Wang Penghui, Xu Xinhua, Gao Qingsong, Au Chaktong, Qiu Renhua. Efficient Synthesis of β-Amino Alcohols Promoted by Triphenylbismuth Bisperfluorooctanesulfonates [J]. Chin. J. Org. Chem., 2016, 36(5): 1094-1098.
[15]	Wang Kehu, Yin Xuejiao, Tao Rui, Huang Danfeng, Su Yingpeng, Hu Yulai, Fu Ying, Du Zhengyin, Wang Jinxian. Study on the Grinding-Induced Solvent-Free Preparation of 3-Styryl-1,5-diketones [J]. Chin. J. Org. Chem., 2016, 36(1): 113-120.

无溶剂条件下合成顺/反3-芳基亚甲基-2,3-二氢-吲哚-2-酮类化合物

Facile Synthesis of Z/E-3-Arylmethylidene-2,3-dihydroindol-2-one under Solvent-Free Conditions

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments