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
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
[11]   Recent progress in the pharmacology of imidazo[1,2-a]pyridines [J].
Enguehard-Gueiffier, Cecile ;
Gueiffier, Alain .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (09) :888-899
[12]   Electrochemically initiated intermolecular C-N formation/cyclization of ketones with 2-aminopyridines: an efficient method for the synthesis of imidazo[1,2-a]pyridines [J].
Feng, Mei-Lin ;
Li, Shu-Qi ;
He, Hui-Zi ;
Xi, Long-Yi ;
Chen, Shan-Yong ;
Yu, Xiao-Qi .
GREEN CHEMISTRY, 2019, 21 (07) :1619-1624
[13]   An efficient 3-acylquinoline synthesis from acetophenones and anthranil via C(sp3)-H bond activation mediated by Selectfluor [J].
Gao, Yejun ;
Hider, Robert C. ;
Ma, Yongmin .
RSC ADVANCES, 2019, 9 (18) :10340-10344
[14]   Synthesis and antiviral activity of novel erythrofuranosyl imidazo[1,2-a]pyridine C-nucleosides constructed via palladium coupling of iodoimidazo[1,2-a]pyridines and dihydrofuran [J].
Gudmundsson, KS ;
Williams, JD ;
Drach, JC ;
Townsend, LB .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (08) :1449-1455
[15]   I2-Catalyzed intramolecular dehydrogenative aminooxygenation of alkynes to acylated imidazo [1,2-a]pyridines and indolizines [J].
He, Yimiao ;
Yin, Wenqing ;
Wang, Jian ;
Huang, Jianrong ;
Pang, Xinru ;
Gan, Chunfang ;
Yang, Fang ;
Huang, Chusheng .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (11) :1772-1776
[16]   I2-catalyzed intramolecular oxidative amination of C(sp3)-H bond: efficient access to 3-acylimidazo [1,2-a]pyridines under neat condition [J].
Huang, Lilan ;
Yin, Wenqing ;
Wang, Jian ;
Gan, Chunfang ;
Huang, Yanmin ;
Huang, Chusheng ;
He, Yimiao .
RSC ADVANCES, 2019, 9 (05) :2381-2385
[17]   Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents [J].
Ismail, MA ;
Brun, R ;
Wenzler, T ;
Tanious, FA ;
Wilson, WD ;
Boykin, DW .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (14) :3658-3664
[18]   Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydroimidazo[1,2-a]pyridines [J].
Ismail, Mohamed A. ;
Arafa, Reem K. ;
Wenzler, Tanja ;
Brun, Reto ;
Tanious, Farial A. ;
Wilson, W. David ;
Boykin, David W. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (02) :683-691
[19]   Oxidative Annulations Involving DMSO and Formamide: K2S2O8 Mediated Syntheses of Quinolines and Pyrimidines [J].
Jadhav, Santosh D. ;
Singh, Anand .
ORGANIC LETTERS, 2017, 19 (20) :5673-5676
[20]   Photocatalyst-free decarboxylative aminoalkylation of imidazo[1,2-a]pyridines with N-aryl glycines enabled by visible light [J].
Ji, Jiu-Jian ;
Zhu, Zhi-Qiang ;
Xiao, Li-Jin ;
Guo, Dong ;
Zhu, Xiao ;
Tang, Juan ;
Wu, Jun ;
Xie, Zong-Bo ;
Le, Zhang-Gao .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21) :3693-3697