Gold-catalyzed formal (3+2) and (4+2) cycloadditions of alkynes to highly functionalized dihydropyrroles and tetrahydropyridines

被引:7
作者
Zhang, Xiao-Qian [1 ]
Xu, Tianyi [1 ]
Zhang, Congdi [1 ]
Wang, Chao [1 ]
Wang, Youliang [1 ]
机构
[1] Xian Jiaotong Univ XJTU, Sch Chem, MOE Key Lab Nonequilibrium Synth & Modulat Condens, Xian Key Lab Sustainable Energy Mat Chem, Xian 710049, Peoples R China
关键词
INTERMOLECULAR 2+2 CYCLOADDITION; RADICAL-ADDITION; HYDROAMINATION; ALKALOIDS; ACETYLENE; EFFICIENT; YNAMIDES;
D O I
10.1039/d2qo01569b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a gold-catalyzed formal cycloaddition reaction of readily available alkynes using amino but/pent-2-enoate derivatives as annulating reagents. The new strategy provides a straightforward and convergent route towards the synthesis of highly functionalized 2,3-dihydropyrroles and 1,2,3,4-tetrahydropyridines with high efficiency and a broad substrate scope. Moreover, the reaction could be facilely performed at the millimole scale and the products could be further transformed into other valuable classes of N-heterocycles.
引用
收藏
页码:680 / 685
页数:6
相关论文
共 62 条
[1]   Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals [J].
Abu Sohel, Shariar Md. ;
Liu, Rai-Shung .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2269-2281
[2]   Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones [J].
Alfonsi, M ;
Arcadi, A ;
Aschi, M ;
Bianchi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2265-2273
[3]   Gold-catalyzed synthesis of 2-substituted, 2,3-Disubstituted and 1,2,3-trisubstituted Indoles in [bmim]BF4 [J].
Ambrogio, Ilaria ;
Arcadi, Antonio ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Marinelli, Fabio .
SYNLETT, 2007, (11) :1775-1779
[4]   Gold-catalysed reactions of diynes [J].
Asiri, Abdullah M. ;
Hashmi, A. Stephen K. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) :4471-4503
[5]   Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes [J].
Bai, Yu-Bin ;
Luo, Zaigang ;
Wang, Yuguang ;
Gao, Jin-Ming ;
Zhang, Liming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (17) :5860-5865
[6]   Electrophilic alkynylation: the dark side of acetylene chemistry [J].
Brand, Jonathan P. ;
Waser, Jerome .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179
[7]   Gold Catalysis Coupled with Visible Light Stimulation: Syntheses of Functionalized Indoles [J].
Cai, Shunyou ;
Yang, Kai ;
Wang, David Zhigang .
ORGANIC LETTERS, 2014, 16 (10) :2606-2609
[8]   Access to Quinolines through Gold-Catalyzed Intermolecular Cycloaddition of 2-Aminoaryl Carbonyls and Internal Alkynes [J].
Cai, Shuting ;
Zeng, Jing ;
Bai, Yaguang ;
Liu, Xue-Wei .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :801-807
[9]   Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes [J].
Campeau, Dominic ;
Rayo, David F. Leon ;
Mansour, Ali ;
Muratov, Karim ;
Gagosz, Fabien .
CHEMICAL REVIEWS, 2021, 121 (14) :8756-8867
[10]   Gold(I)-Catalyzed Formation of 3-Pyrazolines through Cycloaddition of Diaziridine to Alkynes [J].
Capretto, David A. ;
Brouwer, Chad ;
Poor, Catherine B. ;
He, Chuan .
ORGANIC LETTERS, 2011, 13 (21) :5842-5845