Copper-Catalyzed [3+2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones

被引：0

作者：

Hu, Zi-Jun ^{[1
]}

Chen, Wei ^{[2
]}

Lyu, Xinyu ^{[1
]}

Zhang, Hui-Peng ^{[1
]}

Chen, Si-Wei ^{[1
]}

Ding, Xian-Heng ^{[1
]}

Yu, Cang-Hai ^{[1
]}

Cui, Zhen ^{[1
]}

Miao, Chun-Bao ^{[1
]}

Yang, Hai-Tao ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Jiangsu, Peoples R China

[2] Changzhou Siyao Pharmaceut Co Ltd, Changzhou 213018, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 20期

关键词：

INDOLES; ACID;

D O I：

10.1021/acs.orglett.4c01071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed [3 + 2] annulation of O-acyl oximes with 4-sulfonamidophenols is developed. The advantage of this method lies in the concurrent double activation of two substrates to form nucleophilic enamines and electrophilic quinone monoimines. The substituent on the alpha-carbon of O-acyl oxime determines two different reaction pathways, thereby leading to the selective generation of 5-sulfonamidoindoles and 2-amido-5-sulfonamidobenzofuran-3(2H)-ones.

引用

页码：4229 / 4234

页数：6

共 50 条

[31] Palladium-Catalyzed Synthesis of 1,2,3,4-Tetrahydro-5H-2-benzazepin-5-ones
Okuro, Kazumi
Alper, Howard
[J]. SYNLETT, 2012, (17) : 2531 - 2533
[32] Silver-Catalyzed Intermolecular [3+2]/[5+2] Annulation of N-Arylpropiolamides with Vinyl Acids: Facile Synthesis of Fused 2H-Benzo[b]azepin-2-ones
Li, Yang
Hu, Ming
Li, Jin-Heng
[J]. ACS CATALYSIS, 2017, 7 (10): : 6757 - 6761
[33] Silver-Assisted [3+2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
Shen, Xuanyu
Shatskiy, Andrey
Chen, Yan
Karkas, Markus D.
Wang, Xiang-Shan
Liu, Jian-Quan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3560 - 3567
[34] Regiospecific synthesis of novel 6-amino-5-hydroxypyridazin-3(2H)-ones
Dragovich, Peter S.
Blazel, Julie K.
Dao, Kimkim
Ellis, David A.
Li, Lian-Sheng
Murphy, Douglas E.
Ruebsam, Frank
Tran, Chinh V.
Zhou, Yuefen
[J]. SYNTHESIS-STUTTGART, 2008, (04): : 610 - 616
[35] Synthesis of Phenanthridin-6(5H)-ones via Copper-Catalyzed Cyclization of 2-Phenylbenzamides
Gui, Qingwen
Yang, Zhiyong
Chen, Xiang
Liu, Jidan
Tan, Ze
Guo, Ruqing
Yu, Wei
[J]. SYNLETT, 2013, 24 (08) : 1016 - 1020
[36] Synthesis of 2,4-Disubstituted Oxazoles by a Copper-Catalyzed [3+2] Annulation/Olefination Cascade between Amides and IIII /PV Hybrid Ylides
Ye, Xingchen
Wang, Zhaofeng
[J]. SYNLETT, 2024, 35 (10) : 1153 - 1159
[37] Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O-Spiroketal and Spiroketal
Cheng, Wen-Fu
Gao, Shan-Zeng
Yang, Yu-Chen
Wang, Lijia
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (44)
[38] Generation of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones via copper-catalyzed annulation-cyanotrifluoromethylation of 1,7-enynes
Ji, Wen-Zhe
Shi, Hao-Nan
Hao, Wen-Juan
Wei, Ping
Tu, Shu-Jiang
Jiang, Bo
[J]. TETRAHEDRON LETTERS, 2021, 64
[39] HYDROXYIMINO-3(2H)-ISOQUINOLINONES .2. A CONVENIENT METHOD FOR THE PREPARATION OF 4-(HYDROXYIMINO)-1,4-DIHYDRO-3(2H)-ISOQUINOLINONES AND THEIR O-ALKYL AND O-ACYL DERIVATIVES
TIKK, I
DEAK, G
TOTH, G
[J]. ACTA CHIMICA HUNGARICA-MODELS IN CHEMISTRY, 1983, 114 (01): : 69 - 77
[40] Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones
Miao, Chun-Bao
Zheng, An-Qi
Zhou, Li-Jin
Lyu, Xinyu
Yang, Hai-Tao
[J]. ORGANIC LETTERS, 2020, 22 (09) : 3381 - 3385

← 1 2 3 4 5 →