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

被引：10

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

页码：3780 / 3787

页数：8

共 36 条

[1] Arylsulfonamides and selectivity of matrix metalloproteinase-2: An overview
Adhikari, Nilanjan
Mukherjee, Avinaba
Saha, Achintya
Jha, Tarun
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 129 : 72 - 109
[2] The periodic table of the elements of green and sustainable chemistry
Anastas, Paul T.
Zimmerman, Julie B.
[J]. GREEN CHEMISTRY, 2019, 21 (24) : 6545 - 6566
[3] Cobalt-Catalyzed Direct Arylation of Imidazo[1,2-a]pyridine with Aryl Iodides
Babar, Dattatraya A.
Rode, Haridas B.
[J]. 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
Batra, Aanchal
Singh, Kamal Nain
[J]. 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
Bin Sayeed, Ibrahim
Vishnuvardhan, M. V. P. S.
Nagarajan, Apoorva
Kantevari, Srinivas
Kamal, Ahmed
[J]. 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
Cao, Hua
Zhan, Haiying
Lin, Yuanguang
Lin, Xiulian
Du, Zuodong
Jiang, Huanfeng
[J]. ORGANIC LETTERS, 2012, 14 (07) : 1688 - 1691
[7] What Do Patents Tell Us about the Implementation of Green and Sustainable Chemistry?
Constable, David J. C.
[J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (39): : 14657 - 14667
[8] Transition-metal-free B-B and B-interelement reactions with organic molecules
Cuenca, Ana B.
Shishido, Ryosuke
Ito, Hajime
Fernandez, Elena
[J]. 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
Dai, Chenshu
Wang, Junqi
Deng, Siqi
Zhou, Candong
Zhang, Wenhe
Zhu, Qiuhua
Tang, Xiaodong
[J]. RSC ADVANCES, 2017, 7 (57): : 36112 - 36116
[10] Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones
Deng, Siqi
Liang, En
Wu, Yinrong
Tang, Xiaodong
[J]. TETRAHEDRON LETTERS, 2018, 59 (44) : 3955 - 3957

← 1 2 3 4 →