I2 -Catalyzed Three-Component Consecutive Reaction for the Synthesis of 3-Aroylimidazo[1,2-a]-N-Heterocycles

被引：29
作者：
Zhang, Yi [1 ,2 ,3 ]
Chen, Rener [1 ,2 ]
Wang, Zhiming [1 ,2 ]
Wang, Lei [1 ,2 ]
Ma, Yongmin [1 ,2 ,3 ]
机构：
[1] Taizhou Univ, Inst Adv Studies, Taizhou 318000, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 318000, Peoples R China
[3] Zhejiang Chinese Med Univ, Sch Pharmaceut Sci, Hangzhou 310053, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 09期
关键词：
DIMETHYL-SULFOXIDE; AMINOOXYGENATION; 2-AMINOPYRIDINES; DERIVATIVES; IMIDAZO; KETONES; ALKYNES; ACCESS;
D O I：
10.1021/acs.joc.1c00023
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient one-pot, three-component reaction has been developed for the synthesis of 3-aroylimidazo[1,2-a]-N-hetero-cycles from aryl ketones and 2-amino-N-heterocycles using dimethyl sulfoxide as a methylene donor. The reaction proceeds smoothly catalyzed by I-2 in the presence of K2S2O8 and affords the desired products in moderate to good yields. This protocol offers significant superiority in accessing biologically active 3-aroylimidazo[1,2-a]-N-heterocycles with various substitution patterns.
引用
收藏
页码：6239 / 6246
页数：8
相关论文
共 43 条
[1]   Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities [J].
Akhtar, Jawaid ;
Khan, Ahsan Ahmed ;
Ali, Zulphikar ;
Haider, Rafi ;
Yar, M. Shahar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 125 :143-189
[2]   DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].
ALMIRANTE, L ;
POLO, L ;
MUGNAINI, A ;
PROVINCIALI, E ;
RUGARLI, P ;
BIANCOTTI, A ;
GAMBA, A ;
MURMANN, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+
[3]   A One Pot Synthesis of Novel Bioactive Tri-Substitute-Condensed-Imidazopyridines that Targets Snake Venom Phospholipase A2 [J].
Anilkumar, Nirvanappa C. ;
Sundaram, Mahalingam S. ;
Mohan, Chakrabhavi Dhananjaya ;
Rangappa, Shobith ;
Bulusu, Krishna C. ;
Fuchs, Julian E. ;
Girish, Kesturu S. ;
Bender, Andreas ;
Basappa ;
Rangappa, Kanchugarakoppal S. .
PLOS ONE, 2015, 10 (07)
[4]   Synthesis of imidazo[1,2-a]pyridines: a decade update [J].
Bagdi, Avik Kumar ;
Santra, Sougata ;
Monir, Kamarul ;
Hajra, Alakananda .
CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575
[5]   Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines [J].
Basilio-Lopes, Alexandra ;
de Aquino, Thiago Mendonca ;
Mongeot, Alexandre ;
Bourguignon, Jean-Jacques ;
Schmitt, Martine .
TETRAHEDRON LETTERS, 2012, 53 (21) :2583-2587
[6]   1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].
Bozorov, Khurshed ;
Zhao, Jiangyu ;
Aisa, Haji A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531
[7]   Transition Metal-Mediated C=O and C=C Bond-Forming Reactions: A Regioselective Strategy for the Synthesis of Imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrazines [J].
Cao, Hua ;
Liu, Xiaohang ;
Liao, Jinqiang ;
Huang, Jianping ;
Qiu, Huifang ;
Chen, Qinlin ;
Chen, Yaoyi .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22) :11209-11214
[8]   Lewis Acid-Catalyzed Intermolecular Annulation: Three-Component Reaction toward Imidazo[1,2-a]pyridine Thiones [J].
Chen, Zhengwang ;
Liang, Pei ;
Xu, Fan ;
Qiu, Rulin ;
Tan, Qi ;
Long, Lipeng ;
Ye, Min .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (14) :9369-9377
[9]   Iron(III)-catalyzed synthesis of 3-aroylimidazo[1,2-a]pyridines from 2-aminopyridines and ynals [J].
Chen, Zhengwang ;
Liu, Botao ;
Liang, Pei ;
Yang, Zhixiong ;
Ye, Min .
TETRAHEDRON LETTERS, 2018, 59 (07) :667-670
[10]   General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem [J].
Chernyak, Natalia ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) :2743-2746
12345