[Cu(maloNHC)]-catalyzed synthesis of 2-aryl pyrazolo[5,1-a]isoquinolines by annulation of N′-(2-((trimethylsilyflethynyl)benzylidene)hydrazides with terminal aromatic alkynes

被引：11

作者：

Liu, Huixin ^{[1
]}

Lu, Le ^{[1
]}

Hua, Ruimao ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Organ Optoelect & Mol Engn, Minist Educ, Beijing 100084, Peoples R China

来源：

TETRAHEDRON | 2017年 / 73卷 / 45期

基金：

中国国家自然科学基金;

关键词：

Annulation; Alkynes; Pyrazolo[5,1-a]isoquinolines; N-heterocyclic carbene; C-H ACTIVATION; ONE-POT APPROACH; PYRAZOLE DERIVATIVES; CASCADE REACTION; BIOLOGICAL EVALUATION; 3+2 CYCLOADDITION; CLICK CHEMISTRY; EFFICIENT; ISOQUINOLINES; CATALYSIS;

D O I：

10.1016/j.tet.2017.09.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A [Cu(maioNHC)]-catalyzed synthesis of 2-aryl pyrazolo[5,1-a]isoquinolines via annulation of N'-(2((trimethylsilyl)ethynyl)benzylidene)hydrazides with terminal aromatic alkynes was developed. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：6428 / 6435

页数：8

共 54 条

[41] Reusable ammonium salt-tagged NHC-Cu(I) complexes: preparation and catalytic application in the three component click reaction [J].

Wang, Wenlong ;

Wu, Junliang ;

Xia, Chungu ;

Li, Fuwei .

GREEN CHEMISTRY, 2011, 13 (12) :3440-3445

[42] Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution-cyclization-aromatization [J].

Xu, Su-Xia ;

Hao, Lu ;

Wang, Tao ;

Ding, Zong-Cang ;

Zhan, Zhuang-Ping .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (02) :294-298

[43] Cycloaddition of 1,4-Diaryl-1,3-butadiynes with Nitriles: An Atom-economic One-pot Approach to Benzo[f]quinazolines [J].

Yang, Lichen ;

Hua, Ruimao .

CHEMISTRY LETTERS, 2013, 42 (07) :769-771

[44] Cu-Catalyzed alkynylation-cyclization cascade for the construction of thepyrazolo[5,1-a] isoquinoline skeleton [J].

Yang, Yanfang ;

Ren, Hailong ;

Wang, Dongyang ;

Shi, Feng ;

Wu, Chunrui .

RSC ADVANCES, 2013, 3 (26) :10434-10441

[45] Silver triflate-catalyzed three-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and α,β-unsaturated carbonyl compound [J].

Ye, Shengqing ;

Yang, Xiaodi ;

Wu, Jie .

CHEMICAL COMMUNICATIONS, 2010, 46 (29) :5238-5240

[46] Facile Assembly of H-Pyrazolo[5,1-α]isoquinolines via Silver Triflate-Catalyzed One-Pot Tandem Reaction of 2-Alkynyl-benzaldehyde, Sulfonohydrazide, and Ketone or Aldehyde [J].

Yu, Xingxin ;

Ye, Shengqing ;

Wu, Jie .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) :2050-2056

[47] One-Pot Synthesis of Multisubstituted 2-Aminoquinolines from Annulation of 1-Aryl Tetrazoles with Internal Alkynes via Double C-H Activation and Denitrogenation [J].

Zhang, Lei ;

Zheng, Liyao ;

Guo, Biao ;

Hua, Ruimao .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23) :11541-11548

[48] Base-promoted synthesis of 1H,3H-pyrrolo[1,2-c]thiazol-3-imine derivatives via [3+2] annulation of 2-alkynylpyrroles with isothiocyanates [J].

Zhang, Ziyin ;

Guo, Biao ;

Zhou, Yiming ;

Hua, Ruimao .

TETRAHEDRON, 2016, 72 (47) :7613-7619

[49] Synthesis of Natural Product-like Polyheterocycles via One-Pot Cascade Oximation, C-H Activation, and Alkyne Annulation [J].

Zheng, Liyao ;

Bin, Yunhui ;

Wang, Yunpeng ;

Hua, Ruimao .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :8911-8919

[50] Modular Assembly of Ring-Fused and π-Extended Phenanthroimidazoles via C-H Activation and Alkyne Annulation [J].

Zheng, Liyao ;

Hua, Ruimao .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :3930-3936

← 1 2 3 4 5 6 →