Transition Metal Catalyst-Free C-3 Sulfonylmethylation of Imidazo[1,2-a]pyridines with Glyoxylic Acid and Sodium Sulfinates in Water

被引：12

作者：

Chen, Jiewen ^{[1
]}

Wen, Kangmei ^{[1
]}

Wu, Yinrong ^{[1
]}

Shi, Jie ^{[1
]}

Yao, Xingang ^{[1
]}

Tang, Xiaodong ^{[1
]}

机构：

[1] Southern Med Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab New Drug Screening, Guangzhou 510515, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 05期

关键词：

TRIFLUOROMETHYLATION; IMIDAZOHETEROCYCLES; IMIDAZOPYRIDINES; SULFONYLATION; ARYLATION; BROMIDES; ALKENYL; ARYL;

D O I：

10.1021/acs.joc.1c02856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe an efficient and benign protocol for direct C-3 sulfonylmethylation of imidazo[1,2-a]pyridines with glyoxylic acid and sodium sulfinates. Various sulfonylmethylated imidazo[1,2-a]pyridines were synthesized in water under transition metal catalyst-free conditions. This multicomponent reaction featured available substrates, good functional group tolerance, moderate to excellent yields, and mild reaction conditions.

引用

收藏

页码：3780 / 3787

页数：8

相关论文

共 36 条

[1] Arylsulfonamides and selectivity of matrix metalloproteinase-2: An overview [J].

Adhikari, Nilanjan ;

Mukherjee, Avinaba ;

Saha, Achintya ;

Jha, Tarun .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 129 :72-109

[2] The periodic table of the elements of green and sustainable chemistry [J].

Anastas, Paul T. ;

Zimmerman, Julie B. .

GREEN CHEMISTRY, 2019, 21 (24) :6545-6566

[3] Cobalt-Catalyzed Direct Arylation of Imidazo[1,2-a]pyridine with Aryl Iodides [J].

Babar, Dattatraya A. ;

Rode, Haridas B. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (12) :1823-1827

[4] Recent Developments in Transition Metal-Free Cross-Dehydrogenative Coupling Reactions for C-C Bond Formation [J].

Batra, Aanchal ;

Singh, Kamal Nain .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (43) :6676-6703

[5] Imidazopyridine linked triazoles as tubulin inhibitors, effectively triggering apoptosis in lung cancer cell line [J].

Bin Sayeed, Ibrahim ;

Vishnuvardhan, M. V. P. S. ;

Nagarajan, Apoorva ;

Kantevari, Srinivas ;

Kamal, Ahmed .

BIOORGANIC CHEMISTRY, 2018, 80 :714-720

[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] What Do Patents Tell Us about the Implementation of Green and Sustainable Chemistry? [J].

Constable, David J. C. .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (39) :14657-14667

[8] Transition-metal-free B-B and B-interelement reactions with organic molecules [J].

Cuenca, Ana B. ;

Shishido, Ryosuke ;

Ito, Hajime ;

Fernandez, Elena .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (02) :415-430

[9] Acid-mediated sulfonylation of arylethynylene bromides with sodium arylsulfinates: synthesis of (E)-1,2-bis(arylsulfonyl)ethylenes and arylacetylenic sulfones [J].

Dai, Chenshu ;

Wang, Junqi ;

Deng, Siqi ;

Zhou, Candong ;

Zhang, Wenhe ;

Zhu, Qiuhua ;

Tang, Xiaodong .

RSC ADVANCES, 2017, 7 (57) :36112-36116

[10] Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones [J].

Deng, Siqi ;

Liang, En ;

Wu, Yinrong ;

Tang, Xiaodong .

TETRAHEDRON LETTERS, 2018, 59 (44) :3955-3957

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