Facile construction of novel imidazolidine-spirooxindoles via diastereoselective cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles

被引：10

作者：

Zhao, Hong-Wu ^{[1
]}

Li, Bo ^{[1
]}

Tian, Ting ^{[1
]}

Song, Xiu-Qing ^{[1
]}

Pang, Hai-Liang ^{[1
]}

Chen, Xiao-Qin ^{[1
]}

Yang, Zhao ^{[1
]}

Meng, Wei ^{[1
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, 100 Pingleyuan, Beijing 100124, Peoples R China

来源：

RSC ADVANCES | 2016年 / 6卷 / 33期

关键词：

ADDITION/CYCLIZATION CASCADE REACTION; HIGHLY EFFICIENT; STEREOSELECTIVE CONSTRUCTION; ISOTHIOCYANATO OXINDOLES; ASYMMETRIC-SYNTHESIS; CYCLIZATION REACTION; STEREOCENTERS; ANTAGONISTS; KETONES;

D O I：

10.1039/c6ra01962e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of 10 mol% of Na2CO3, the desired imidazolidine-spirooxindoles were obtained in 81-99% yield with up to 99 : 1 dr by means of the diastereoselective [3 + 2] cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles. Single-crystal X-ray structure analysis was conducted to determine the relative stereochemistry of the imidazolidine-spirooxindoles. Diastereoselective access to the imidazolidine-spirooxindoles was hypothesized by the proposed mechanism.

引用

页码：27690 / 27695

页数：6

共 4 条

[1] Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3+2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles
Zhao, Hong-Wu
Tian, Ting
Li, Bo
Yang, Zhao
Pang, Hai-Liang
Meng, Wei
Song, Xiu-Qing
Chen, Xiao-Qin
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 10380 - 10385
[2] Stereo- and Regioselective Construction of Spirooxindoles Having Continuous Spiral Rings via Asymmetric [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Thioaurone Derivatives
Gui, Hou-Ze
Meng, Zhe
Xiao, Zhan-Shuai
Yang, Ze-Ren
Wei, Yin
Shi, Min
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (42) : 6614 - 6622
[3] Construction of Novel Tetrahydro--carboline-1-thione Spirooxindoles by BrOnsted Acid Mediated Formal [3+3] Cyclization of 3-Indolylmethanols with 3-Isothiocyanato Oxindoles
Liao, Yijun
Bai, Mei
Yu, Shuowen
Zhang, Minmin
Hu, Fangzhi
Xu, Xiaoying
Yuan, Weicheng
Zhang, Xiaomei
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) : 1311 - 1317
[4] A novel and diastereoselective construction of H-pyrazolo [3,2-a]isoquinoline fused spirooxindoles via [3+2] cycloaddition
Yuvaraj, Panneerselvam
Reddy, Boreddy S. R.
TETRAHEDRON LETTERS, 2014, 55 (04) : 806 - 810

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