Catalyst-Free [3+2] Cycloaddition of Electron-Deficient Alkynes and o-Hydroxyaryl Azomethine Ylides in Water

被引：8

作者：

Zhu, Jin ^{[1
]}

Su, Wenbo ^{[1
]}

Xiong, Cheng ^{[1
]}

Bai, Ruifang ^{[1
]}

Zhou, Qingfa ^{[1
]}

Chen, Ming ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Peoples R China

来源：

ACS OMEGA | 2020年 / 5卷 / 29期

基金：

中国国家自然科学基金;

关键词：

1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; CONSTRUCTION; HETEROCYCLES; DERIVATIVES; PAX3-FOXO1; ESTERS;

D O I：

10.1021/acsomega.0c01856

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalyst-free [3 + 2] cycloaddition reaction of electron-deficient alkynes and o-hydroxyaryl azomethine ylides in water was developed, affording pyrroline derivatives in moderate to high yields (up to 90%).

引用

页码：18244 / 18253

页数：10

共 50 条

[31] Rhodium-Catalyzed Intermolecular [2+2] Cycloaddition of Terminal Alkynes with Electron-Deficient Alkenes [J].

Sakai, Kazunori ;

Kochi, Takuya ;

Kakiuchi, Fumitoshi .

ORGANIC LETTERS, 2013, 15 (05) :1024-1027

[32] Asymmetric BrOnsted Base Catalyzed and Directed [3+2] Cycloaddition of 2-Acyl Cycloheptatrienes with Azomethine Ylides [J].

Lauridsen, Vibeke H. ;

Ibsen, Lise ;

Blom, Jakob ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) :3259-3263

[33] Tandem [3+2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines [J].

Jia, Hao ;

Liu, Honglei ;

Guo, Zhenyan ;

Huang, Jiaxing ;

Guo, Hongchao .

ORGANIC LETTERS, 2017, 19 (19) :5236-5239

[34] Catalyst-Controlled Chemodivergent [3+3] and [3+2] Formal Cycloadditions of Azomethine Ylides with Diphenylcyclopropenone [J].

Corpas, Javier ;

Ponce, Alberto ;

Maclean, Ian ;

Adrio, Javier ;

Carretero, Juan C. .

SYNTHESIS-STUTTGART, 2022, 54 (21) :4673-4682

[35] Formal [3+2] cycloaddition of azomethine ylides generated in situ with unactivated cyclic imines: A facile approach to tricyclic imidazolines derivatives [J].

Wang, Kai-Kai ;

Li, Yan-Li ;

Wang, Zhan-Yong ;

Ma, Xueji ;

Mei, Ya-Lei ;

Zhang, Shan-Shan ;

Chen, Rongxiang .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (03) :1456-1463

[36] Revealing the mechanism, Regio- and stereo selectivity and solvent effects of [3+2] cycloaddition reactions involving N-benzyl fluoro nitrone and electron-deficient alkynes [J].

Boutiddar, Rachid ;

Abbiche, Khalid ;

Izzaouihda, Safia ;

Taleb, Abdelaziz Ait ;

El Baraka, Noureddine ;

Errai, Mohamed ;

Makarim, Hassna Abou El ;

El Hammadi, Abdellatif ;

Hochlaf, Majdi .

COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2024, 1237

[37] [3+2] cycloaddition of quinazoline-derived azomethine imines with electron-deficient alkenes to access functionalized fused tricyclic tetrahydropyrazolo[1,5-c]quinazoline frameworks [J].

Wang, Kai-Kai ;

Li, Ya-Fei ;

Bi, Ran ;

Wang, Xue-Hao ;

Xue, Xue ;

Lu, Peng ;

Ma, Yue-Yao ;

Zhao, Na-Na ;

Yan, Guo-Yi .

TETRAHEDRON, 2025, 184

[38] Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides [J].

Brioche, Julien ;

Meyer, Christophe ;

Cossy, Janine .

ORGANIC LETTERS, 2015, 17 (11) :2800-2803

[39] One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3+2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions [J].

Ma, Xiaoming ;

Zhang, Xiaofeng ;

Qiu, Weiqi ;

Zhang, Wensheng ;

Wan, Bruce ;

Evans, Jason ;

Zhang, Wei .

MOLECULES, 2019, 24 (03)

[40] L-tert-Leucine-Derived AmidPhos-Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides [J].

Zhou, Zhipeng ;

Zheng, Xiaojun ;

Liu, Jialin ;

Li, Jinlei ;

Wen, Pushan ;

Wang, Haifei .

SYNLETT, 2017, 28 (08) :999-1003

← 1 2 3 4 5 →