A copper-catalyzed oxidative intramolecular cyclization approach for the synthesis of mesoionic [1,2,3]triazo[5,1-a]isoquinoliums

被引：3

作者：

Zhang, Wen ^{[1
]}

Wu, Yangang ^{[1
]}

Song, Chuanjun ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China

来源：

TETRAHEDRON LETTERS | 2023年 / 115卷

关键词：

Copper catalysis; 6-endo-Dig cyclization; C-H bond oxidation; Mesoionic; 1; 2; 3]triazo[5; 1-a]isoquinolium; FACILE SYNTHESIS; CASCADE; TRIAZOLOPYRIDINES; CYCLOADDITION; ISOQUINOLINES; DERIVATIVES; ACCESS; ROUTE; AZIDE;

D O I：

10.1016/j.tetlet.2022.154333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1-alkyl-4-(2-alkynylphenyl)triazoles with copper acetate resulted in the formation of mesoionic [1,2,3]triazo[5,1-a]isoquinoliums via 6-endo-dig cyclization and C-H bond oxidation.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：4

共 26 条

[11] Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision [J].

Gulevskaya, Anna V. ;

Tyaglivy, Alexander S. ;

Pozharskii, Alexander F. ;

Nelina-Nemtseva, Julia I. ;

Steglenko, Dmitry V. .

ORGANIC LETTERS, 2014, 16 (06) :1582-1585

[12] Copper-catalyzed tandem synthesis of [1,2,3]triazolo[5,1-a]isoquinolines and their transformation to 1,3-disubstituted isoquinolines [J].

Hu, Yuan-Yuan ;

Hu, Jie ;

Wang, Xiang-Chuan ;

Guo, Li-Na ;

Shu, Xing-Zhong ;

Niu, Yan-Ning ;

Liang, Yong-Min .

TETRAHEDRON, 2010, 66 (01) :80-86

[13] Synthesis and fungicidal activity of monocyclic and fused 1,2,3-triazolium-5-olates [J].

Khazhieva, Inna S. ;

Demkin, Pavel M. ;

Eltsov, Oleg S. ;

Nein, Yulia I. ;

Kalinina, Tatiana A. ;

Fan, Zhi-Jin ;

Chen, Lai ;

Zhao, Bin ;

Glukhareva, Tatiana V. ;

Morzherin, Yuri Yu. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (10) :956-963

[14] Rapid Access to Novel 1,2,3-Triazolo-Heterocyclic Scaffolds via Tandem Knoevenagel Condensation/Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in One Pot [J].

Maurya, Ram Awatar ;

Adiyala, Praveen Reddy ;

Chandrasekhar, D. ;

Reddy, Chada Narsimha ;

Kapure, Jeevak Sopanrao ;

Kamal, Ahmed .

ACS COMBINATORIAL SCIENCE, 2014, 16 (09) :466-477

[15] Silver-Catalyzed Tandem Hydroazidation/Alkyne-Azide Cycloaddition of Diynes with TMS-N3: An Easy Access to 1,5-Fused 1,2,3-Triazole Frameworks [J].

Ning, Yongquan ;

Wu, Nannan ;

Yu, Haifeng ;

Liao, Peiqiu ;

Li, Xingqi ;

Bi, Xihe .

ORGANIC LETTERS, 2015, 17 (09) :2198-2201

[16] CONDENSED ISOQUINOLINES .14. SYNTHESIS OF UPSILON-TRIAZOLO[5,1-ALPHA]ISOQUINOLINES [J].

REIMLINGER, H ;

LINGIER, WRF ;

MERENYI, R .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (12) :3794-3798

[17] Water soluble triazolopyridiniums as tunable blue light emitters [J].

Su, Xin ;

Liptak, Matthew D. ;

Aprahamian, Ivan .

CHEMICAL COMMUNICATIONS, 2013, 49 (39) :4160-4162

[18] SYNTHESIS OF [1,2,3]TRIAZOLO[5,1-a]ISOQUINOLINE DERIVATIVES VIA A SELECTIVE CASCADE CYCLIZATION SEQUENCE OF 1,2-BIS (PHENYLETHYNYL)BENZENE DERIVATIVES [J].

Tao, Shipeng ;

Hu, Qinquan ;

Li, Huan ;

Ma, Shan ;

Chen, Yunfeng .

SYNTHETIC COMMUNICATIONS, 2015, 45 (11) :1354-1361

[19] 2H-Bis-1,2,3-triazolo-isoquinoline: Design, Synthesis, and Photophysical Study [J].

Tsyrenova, Biligma ;

Khrustalev, Victor ;

Nenajdenko, Valentine .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) :7024-7035

[20] Fused mesoionic heterocyclic compounds are a new class of aryl hydrocarbon receptor (AhR) agonist of exceptional potency [J].

Wall, Richard J. ;

Bell, David R. ;

Bazzi, Rana ;

Fernandes, Alwyn ;

Rose, Martin ;

Rowlands, J. Craig ;

Mellor, Ian R. .

TOXICOLOGY, 2012, 302 (2-3) :140-145

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