Aerobic Multicomponent Tandem Synthesis of 3-Sulfenylimidazo[1,2-a] pyridines from Ketones, 2-Aminopyridines, and Disulfides

被引：103

作者：

Ge, Wenlei ^{[1
]}

Zhu, Xun ^{[1
,2
]}

Wei, Yunyang ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

[2] Yancheng Inst Ind Technol, Dept Chem Engn, Yancheng, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 27期

关键词：

Multicomponent reactions; Tandem reactions; C-H functionalization; Cerium; Sulfur; Ketones; ONE-POT SYNTHESIS; CATALYZED OXIDATIVE SYSTEM; COUPLING REACTION; C-C; EFFICIENT PROCEDURE; PALLADIUM; INDOLES; ALDEHYDES; IODINE; 3-SULFENYLATION;

D O I：

10.1002/ejoc.201300905

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An aerobic CeCl3 center dot 7H(2)O/NaI-catalyzed C-H functionalization reaction was developed for the synthesis of 3-sulfenylimidazo[1,2-alpha]pyridines from easily available ketones, 2-aminopyridines, and disulfides without DMSO or peroxide as an oxidant. This three-component tandem reaction process involves the formation of imidazo[1,2-alpha]pyridines followed by Friedel-Crafts sulfenylation in one pot under mild conditions. Both aryl and alkyl ketones afforded the desired products in good to excellent yields without the presence of other additives.

引用

页码：6015 / 6020

页数：6

共 50 条

[11] Zinc Iodide Catalyzed Synthesis of 3-Aminoimidazo[1,2-a]pyridines from 2-Aminopyridines and α-Amino Carbonyl Compounds
Han, Xu
Ma, Chaowei
Wu, Zhaoyang
Huang, Guosheng
SYNTHESIS-STUTTGART, 2016, 48 (03): : 351 - 356
[12] Graphene oxide (GO)-catalyzed multi-component reactions: green synthesis of library of pharmacophore 3-sulfenylimidazo[1,2-a]pyridines
Kundu, Samir
Basu, Basudeb
RSC ADVANCES, 2015, 5 (62): : 50178 - 50185
[13] Electrochemically initiated intermolecular C-N formation/cyclization of ketones with 2-aminopyridines: an efficient method for the synthesis of imidazo[1,2-a]pyridines
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
[14] PYRIDO[1,2-A]PYRIMIDINIUM SALTS .1. SYNTHESIS FROM 2-AMINOPYRIDINES AND INTERCONVERSION WITH 2-(2-ACYLVINYLAMINO)PYRIDINES
SAWYER, JRH
WIBBERLEY, DG
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (11): : 1138 - 1143
[15] CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines
Bharate, Jaideep B.
Abbat, Sheenu
Bharatam, Prasad V.
Vishwakarma, Ram A.
Bharate, Sandip B.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) : 7790 - 7794
[16] One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides
Adib, Mehdi
Sheikhi, Ehsan
Rezaei, Narjes
TETRAHEDRON LETTERS, 2011, 52 (25) : 3191 - 3194
[17] Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
Liu, Yanpeng
Lu, Lixue
Zhou, Haipin
Xu, Feijie
Ma, Cong
Huang, Zhangjian
Xu, Jinyi
Xu, Shengtao
RSC ADVANCES, 2019, 9 (59) : 34671 - 34676
[18] Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines
Adiyala, Praveen Reddy
Mani, Geeta Sai
Nanubolu, Jagadeesh Babu
Shekar, Kunta Chandra
Maurya, Ram Awatar
ORGANIC LETTERS, 2015, 17 (17) : 4308 - 4311
[19] Visible Light Driven Coupling of 2-aminopyridines and α-Keto Vinyl Azides for the Synthesis of Imidazo[1,2-a]pyridines and Their Cytotoxicity
Adiyala, Praveen Reddy
Sastry, Kasinathuni Naga Visweswara
Kovvuri, Jeshma
Nagarajan, Apoorva
Reddy, Velma Ganga
Bin Sayeed, Ibrahim
Nayak, Vedinthe Lakshma
Maurya, Ram Awatar
Kamal, Ahmed
CHEMISTRYSELECT, 2017, 2 (26): : 8158 - 8161
[20] A Cu(II)-promoted tandem decarboxylative halogenation and oxidative diamination reaction of 2-aminopyridines with alkynoic acids for the synthesis of 2-haloimidazo[1,2-a]pyridines
Liu, Yun
Wang, Wenhui
Han, Junwen
Sun, Jinwei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (44) : 9311 - 9318

← 1 2 3 4 5 →