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
收藏
页码:3685 / 3691
页数:7
相关论文
共 70 条
[1]   Directed Metalation of 1-Ester-Substituted Indolizines: Base/Electrophile-Controlled Regioselective Functionalization [J].
Amaral, Monica F. Z. J. ;
Baumgartner, Amanda A. ;
Vessecchi, Ricardo ;
Clososki, Giuliano C. .
ORGANIC LETTERS, 2015, 17 (02) :238-241
[2]   Synthesis of Ester-Substituted Indolizines from 2-Propargyloxypyridines and 1,3-Dicarbonyls [J].
Anderson, Carolyn E. ;
Bos, Haleigh I. ;
Dreher, Daniel M. ;
Hartgerink, Colin T. ;
Scholtens, Chase J. ;
Staples, Richard J. .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15) :10241-10249
[3]   Lewis Acid Catalyzed Intramolecular [4+2] and [3+2] Cross-Cycloaddition of Alkynylcyclopropane Ketones with Carbonyl Compounds and Imines [J].
Bai, Yu ;
Tao, Weijie ;
Ren, Jun ;
Wang, Zhongwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) :4112-4116
[4]   Highly Diastereoselective Gold- or Copper-Catalyzed Formal [4+3] Cycloaddition of 1-(1-Alkynyl) Cyclopropyl Ketones and Nitrones [J].
Bai, Yu ;
Fang, Jie ;
Ren, Jun ;
Wang, Zhongwen .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (36) :8975-8978
[5]   SYNTHESES OF PYRROCOLINES UNSUBSTITUTED IN THE 5-MEMBERED RING [J].
BOEKELHEIDE, V ;
WINDGASSEN, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (06) :1456-1459
[6]   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
[7]   Catalyst-Dependent Divergent Synthesis of Pyrroles from 3-Alkynyl Imine Derivatives: A Noncarbonylative and Carbonylative Approach [J].
Chen, Gen-Qiang ;
Zhang, Xiao-Nan ;
Wei, Yin ;
Tang, Xiang-Ying ;
Shi, Min .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) :8492-8497
[8]   Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J].
Chen Zuliang ;
Wei Yingjing ;
Zhang Junliang .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) :3078-3088
[9]   Lewis acid-catalyzed [4+2] cycloaddition of donoracceptor cyclobutanes with iminooxindoles: access to spiro[piperidine-3,2'-oxindoles] [J].
Chen, Zuliang ;
Yan, Keyi ;
Luo, Hui ;
Yan, Jun ;
Zeng, Yang .
RSC ADVANCES, 2022, 12 (49) :32097-32101
[10]   Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a stepwise [(5+1)-1] pathway [J].
Cheng, Bin ;
Zhang, Xinping ;
Li, Yuntong ;
Li, Hui ;
He, Yixuan ;
Li, Yun ;
Wang, Taimin ;
Zhai, Hongbin .
CHEMICAL COMMUNICATIONS, 2020, 56 (60) :8396-8399