Gold-catalyzed intermolecular tandem cyclization/[4+3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines

被引：1

作者：

Rao, Fucai ^{[1
]}

Cheng, Meng ^{[1
]}

Hu, Zhiwei ^{[1
]}

Chen, Xinyi ^{[1
]}

Zhao, Suyang ^{[1
]}

Chen, Zuliang ^{[1
,2
]}

机构：

[1] Yichun Univ, Coll Chem & Bioengn, Yichun 336000, Peoples R China

[2] Yichun Univ, Key Lab Jiangxi Univ Appl Chem & Chem Biol, Yichun 336000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 13期

基金：

中国国家自然科学基金;

关键词：

1,3-DIPOLAR CYCLOADDITION; 1-(1-ALKYNYL)CYCLOPROPYL KETONES; MODULAR ENTRY; CYCLIZATION; 2-(2-ENYNYL)PYRIDINES; CYCLOBUTANES; DERIVATIVES; DISCOVERY; PYRROLES; ACCESS;

D O I：

10.1039/d4qo00580e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient approach is described for the diastereoselective synthesis of [1,2]oxazepino[5,4-a] indolizines via a gold-catalyzed [4 + 3] cycloaddition reaction of 2-(1-alkynyl)-cyclopropyl pyridine with nitrones. This methodology has great potential to construct seven-membered heterocycle-fused indolizine scaffolds from simple building blocks. Based on our preliminary results, a probable mechanism for this reaction pathway has been proposed.

引用

页码：3685 / 3691

页数：7

共 70 条

[31] Gold(I)-Catalyzed Cascade Hydroarylation/Cycloaromatization to Indolizines via Pyridine Ring Construction [J].

Li, Xiangdong ;

Xie, Xin ;

Liu, Yuanhong .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09) :3688-3699

[32] B2pin2-Mediated Cascade Cyclization/Aromatization Reaction: Facial Access to Functionalized Indolizines [J].

Li, Xiaoning ;

Chen, Zunsheng ;

Chen, Weiming ;

Xie, Xin ;

Zhou, Hui ;

Liao, Yingmei ;

Yu, Fuchao ;

Huang, Jiuzhong .

ORGANIC LETTERS, 2022, 24 (40) :7372-7377

[33] Indolizine synthesis via Cu-catalyzed cyclization of 2-(2-enynyl)pyridines with nucleophiles [J].

Liu, Ren-Rong ;

Cai, Zheng-Yi ;

Lu, Chuan-Jun ;

Ye, Shi-Chun ;

Xiang, Bin ;

Gao, Jianrong ;

Jia, Yi-Xia .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (03) :226-230

[34] Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles [J].

Liu, Ren-Rong ;

Ye, Shi-Chun ;

Lu, Chuan-Jun ;

Xiang, Bin ;

Gao, Jianrong ;

Jia, Yi-Xia .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) :4855-4858

[35] Transition-metal-free synthesis of indolizines via [3+2]-annulation from α-bromoenals and 2-substituted azaarenes [J].

Liu, Yuan ;

Yu, Yang ;

Fu, Yiwei ;

Liu, Yonghai ;

Shi, Lei ;

Li, Hao ;

Wang, Wei .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11) :2119-2123

[36] AgOTf/Et3N Cooperative Catalysis Enabled One-Pot Access to α-(Indolizinylethyl)-Substituted N-Sulfonyl Ketimines via an Imino-Alkyne Cyclization [J].

Lodhi, Rajni ;

Patel, Ashvani K. K. ;

Samanta, Sampak .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)

[37] Indolizine synthesis via copper-catalyzed cyclization of gem-difluoroalkenes and 2-(pyridin-2-yl)acetate derivatives [J].

Lu, Chuan-Jun ;

Yu, Xin ;

Chen, Yu-Ting ;

Song, Qing-Bao ;

Wang, Hong .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (16) :2313-2318

[38] A Practical Method for the Synthesis of Donor-Acceptor Cyclobutanes by Cu(OAc)2 or FeCl3 Catalyzed [2+2] Cycloaddition [J].

Luo, Hui ;

Yan, Jun ;

Chen, Zuliang ;

Wei, Yingjing ;

Chen, Bin ;

Liu, Yu .

CHEMISTRYSELECT, 2020, 5 (13) :4074-4077

[39] Cu-Catalyzed Hydrophosphonylation of 2-(2-Enynyl)pyridines: Easy Access to Indolizine-Containing Diarylmethylphosphonates [J].

Mahesh, Sriram ;

Anand, Ramasamy Vijaya .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (19) :2698-2706

[40] Catalytic Asymmetric Conjugate Addition of Indolizines to α,β-Unsaturated Ketones [J].

Menezes Correia, Jose Tiago ;

List, Benjamin ;

Coelho, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :7967-7970

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