Construction of pyrazolo[5,1-a]isoindol-8(3aH)-one derivatives via phosphine-catalyzed cyclization of electron-deficient alkynes and N-amino substituted phthalimide

被引：16

作者：

Zhou, Qing-Fa ^{[1
,2
]}

Ge, Fei-Fei ^{[1
]}

Chen, Qing-Qing ^{[1
]}

Lu, Tao ^{[1
]}

机构：

[1] China Pharmaceut Univ, Sch Basic Sci, Nanjing 210009, Peoples R China

[2] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Peoples R China

来源：

RSC ADVANCES | 2016年 / 6卷 / 02期

基金：

中国国家自然科学基金;

关键词：

HIGHLY STEREOSELECTIVE-SYNTHESIS; DOMINO REACTION; DIMETHYL ACETYLENEDICARBOXYLATE; ASYMMETRIC-SYNTHESIS; INTRAMOLECULAR CYCLIZATION; THIOPHOSPHINYL IMINES; MEDIATED SYNTHESIS; 3+2 ANNULATIONS; FACILE ENTRY; CYCLOADDITION;

D O I：

10.1039/c5ra17267e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel method for the synthesis of diversely functionalized pyrazolo[5,1-a]isoindol-8(3aH)-ones is developed via phosphine-catalyzed tandem Michael addition/intramolecular Morita-Baylis-Hillman reaction of electron-deficient alkynes and N-amino substituted phthalimide. This cyclization is operationally simple under metal-free reaction conditions.

引用

页码：1395 / 1402

页数：8

共 4 条

[1] Phosphine-Catalyzed [3+2] Annulation of Electron-Deficient Alkynes with N-Hydroxyphthalimide: Synthesis of 3a-Hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones
Zhou, Qing-Fa
Chu, Xue-Ping
Ge, Fei-Fei
Wang, Yue
Lu, Tao
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) : 2787 - 2792
[2] Phosphine-Catalyzed Domino Reactions of Allenoates with N-Hydroxyphthalimides: Direct Method to 3a-Hydroxyisoxazolo[3,2-a]isoindol-8(3 aH)-one Derivatives
Zhao, Shuang
Zhu, Yong
Wu, Yichao
Lu, Tao
Zhou, Qingfa
CHEMISTRYSELECT, 2017, 2 (04): : 1700 - 1704
[3] Copper(I)/phosphine-catalyzed tandem carboxylation/annulation of terminal alkynes under ambient pressure of CO2: one-pot access to 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones
Xie, Jia-Ning
Yu, Bing
Guo, Chun-Xiang
He, Liang-Nian
GREEN CHEMISTRY, 2015, 17 (07) : 4061 - 4067
[4] ALTERNATE SYNTHESIS ROUTE OF 2-(SUBSTITUTED PHENYL)-3,3a-DIHYDRO-8H-PYRAZOLO[5,1-a]ISOINDOL-8-ONES VIA CHALCONE-BASED N-FORMYL-PYRAZOLINES
Ahmed, Naseem
Dev, Dharm
SYNTHETIC COMMUNICATIONS, 2013, 43 (05) : 689 - 704

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