Electrochemically Promoted Three-Component Reaction to N-Sulfonyl Amidines

被引：4

作者：

Zhang, Zhang ^{[1
]}

Meng, Xiu-Jin ^{[2
]}

Cui, Fei-Hu ^{[2
,3
]}

Tang, Hai-Tao ^{[2
]}

Wang, Ying-Chun ^{[1
]}

Huang, Guo-Bao ^{[3
]}

Pan, Ying-Ming ^{[2
]}

机构：

[1] Jishou Univ, Coll Chem & Chem Engn, Jishou 416000, Peoples R China

[2] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, State Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China

[3] Yulin Normal Univ, Coll Chem & Food Sci, Guangxi Key Lab Agr Resources Chem & Biotechnol, Yulin 537000, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 26卷 / 01期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; INHIBITORS; METHANOL;

D O I：

10.1021/acs.orglett.3c03820

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, a multicomponent reaction via the Mannich intermediate was developed using methanol, secondary amine, and sulfonamide as starting materials. This method uses methanol as a green C1 source. The substrate scope is wide, and the yield is good. The mechanistic study shows that methanol generates formaldehyde under electrochemical conditions, and sulfonyl amidine as a nucleophile reacts with Schiff base intermediates to form N-sulfonyl amidine in a single step.

引用

页码：193 / 197

页数：5

共 50 条

[21] N-SULFONYL PYRIDINIUM SALTS IN THE HETARYLATION REACTION
SKRYPNIK, YG
SIDORENKO, LM
SAMOJLENKO, GV
SHEINKMAN, AK
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1979, 6 (1-2): : 287 - 288
[22] Iodine-promoted three-component reaction for the synthesis of spirooxindoles
Zhang, Min
Yang, Wenbo
Qian, Min
Zhao, Ting
Yang, Liuqing
Zhu, Chunyin
[J]. TETRAHEDRON, 2018, 74 (09) : 955 - 961
[23] A carbon dioxide-promoted three-component Strecker reaction
Fauziev, Ruslan, V
Ivanov, Roman E.
Kuchurov, Ilya, V
Zlotin, Sergei G.
[J]. GREEN CHEMISTRY, 2021, 23 (24) : 10137 - 10144
[24] Ferric Perchlorate Promoted Reaction of [60]Fullerene with N-Sulfonyl Aldimines: Synthesis and Functionalization of Fulleroxazolidines
Liu, Tong-Xin
Li, Fa-Bao
Zhou, Dian-Bing
Wang, Guan-Wu
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 11986 - 11992
[25] Palladium-catalyzed three-component reaction of N-tosyl hydrazones, isonitriles and amines leading to amidines
Dai, Qiang
Jiang, Yan
Yu, Jin-Tao
Cheng, Jiang
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (93) : 16645 - 16647
[26] An Efficient Synthesis of N′-(Fluoroalkylsulfonyl) Amidines by a Copper(I)-Catalyzed One-Pot Three-Component Reaction
Xiong, Wanting
Xin, Yong
Zhao, Jingwei
Zhu, Shizheng
[J]. SYNTHESIS-STUTTGART, 2011, (07): : 1142 - 1148
[27] Photoinduced Synthesis of Sulfonyl-Containing Phosphorothioates via a Three-Component Reaction
Wu, Xianda
Chen, Minghong
Zheng, Shuiyun
Wu, Jie
Liu, Gang
He, Fu-Sheng
[J]. MOLECULES, 2023, 28 (23):
[28] Access to Sulfocoumarins by Three-Component Reaction of β-Keto Sulfonyl Fluorides, Arynes, and DMF
Huang, Yuan
Zhao, Xueyan
Chen, Dengfeng
Zheng, Yu
Luo, Jinyue
Huang, Shenlin
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (27)
[29] Three-Component Domino Acylation/Trifluoromethylation of Bicyclic Amidines
Luo, Ziwei
Chen, Jiahua
Li, Mengwan
Tsui, Gavin Chit
[J]. ORGANIC LETTERS, 2023, 25 (30) : 5656 - 5660
[30] REACTION OF N-SULFONYL SULFILIMINE WITH CYANIDE ION IN DMSO
OAE, S
AIDA, T
TSUJIHAR.K
FURUKAWA, N
[J]. TETRAHEDRON LETTERS, 1971, (16) : 1145 - &

← 1 2 3 4 5 →