Iron-Catalyzed Regioselective Alkoxycarbonylation of Imidazoheterocycles with Carbazates

被引:81
作者
Gao, Yongyuan [1 ]
Lu, Weiye [1 ]
Liu, Ping [1 ]
Sun, Peipei [1 ]
机构
[1] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Jiangsu Prov Key Lab Mat Cycle Proc & Pollut Cont, Coll Chem & Mat Sci, Nanjing 210023, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
METAL-FREE; OXIDATIVE ALKOXYCARBONYLATION; CARBONYLATION REACTIONS; DIRECT ARYLATION; ALKENES; C-3; ARYLALKOXYCARBONYLATION; 2-ISOCYANOBIPHENYLS; PHENANTHRIDINES; THIOCYANATION;
D O I
10.1021/acs.joc.6b00046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regioselective alkoxycarbonylation of imidazoheterocycles using carbazates as ester group sources in DMSO was developed, in which an inexpensive FeCl2 center dot 4H(2)O was used as the catalyst and (NH4)(2)S2O8 was the oxidant. The reaction proceeded smoothly under an air atmosphere to give the 3-alkoxycarbonylated products in moderate to good yields.
引用
收藏
页码:2482 / 2487
页数:6
相关论文
共 44 条
[1]   Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate [J].
Bagdi, Avik Kumar ;
Mitra, Shubhanjan ;
Ghosh, Monoranjan ;
Hajra, Alakananda .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) :3314-3320
[2]   Inhibitors of apoptosis in lymphocytes:: Synthesis and biological evaluation of compounds related to pifithrin-α [J].
Barchéchath, SD ;
Tawatao, RI ;
Corr, M ;
Carson, DA ;
Cottam, HB .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (20) :6409-6422
[3]   Palladium-Catalyzed Carbonylation Reactions of Alkenes and Alkynes [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2009, 1 (01) :28-41
[4]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[5]   Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen [J].
Cao, Hua ;
Lei, Sai ;
Li, Naiying ;
Chen, Longbin ;
Liu, Jingyun ;
Cai, Huiyin ;
Qiu, Shuxian ;
Tan, Jingwen .
CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1823-1825
[6]   Direct Arylation of Imidazo[1,2-a]pyridine at C-3 with Aryl Iodides, Bromides, and Triflates via Copper(I)-Catalyzed C-H Bond Functionalization [J].
Cao, Hua ;
Zhan, Haiying ;
Lin, Yuanguang ;
Lin, Xiulian ;
Du, Zuodong ;
Jiang, Huanfeng .
ORGANIC LETTERS, 2012, 14 (07) :1688-1691
[7]   Regioselective Direct C-3 Arylation of Imidazo[1,2-a]pyridines with Aryl Tosylates and Mesylates Promoted by Palladium-Phosphine Complexes [J].
Choy, Pui Ying ;
Luk, Kwan Chak ;
Wu, Yinuo ;
So, Chau Ming ;
Wang, Lai-lai ;
Kwong, Fuk Yee .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) :1457-1463
[8]   Preparation of highly substituted (β-acylamino)acrylates via iron-catalyzed alkoxycarbonylation of N-vinylacetamides with carbazates [J].
Ding, Ran ;
Zhang, Qiu-Chi ;
Xu, Yun-He ;
Loh, Teck-Peng .
CHEMICAL COMMUNICATIONS, 2014, 50 (79) :11661-11664
[9]   Phosphine-Free Palladium-Catalyzed Direct Arylation of Imidazo[1,2-a]pyridines with Aryl Bromides at Low Catalyst Loading [J].
Fu, Hai Yan ;
Chen, Lu ;
Doucet, Henri .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) :4473-4478
[10]   Aerobic Multicomponent Tandem Synthesis of 3-Sulfenylimidazo[1,2-a] pyridines from Ketones, 2-Aminopyridines, and Disulfides [J].
Ge, Wenlei ;
Zhu, Xun ;
Wei, Yunyang .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (27) :6015-6020