Calcium Carbide as a Surrogate of Acetylene: Copper-Catalyzed Construction of 3-Methylene-2-arylisoindolin-1-ones

被引：14

作者：

Liu, Haiyan ^{[1
]}

You, Xinjie ^{[1
]}

Wen, Fei ^{[1
]}

Zhang, Zeshuai ^{[1
]}

Li, Zheng ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Acetylene; alkyne source; calcium carbide; 3-methylene-2-arylisoindolin-1-one; tandem reaction; 1ST TOTAL-SYNTHESIS; ISOINDOLINONE DERIVATIVES; INHIBITORY-ACTIVITY; TERMINAL ALKYNES; SUZUKI-MIYAURA; PALLADIUM-FREE; LIGAND-FREE; 3-METHYLENEISOINDOLIN-1-ONES; ARISTOLACTAMS; AMIDATION;

D O I：

10.1002/ajoc.202200204

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of 3-methylene-2-arylisoindolin-1-ones through Sonogashira cross-coupling/nucleophilic addition tandem reactions using calcium carbide as an alkyne source, 2-bromo-N-arylbenzamides as starting materials and copper as a catalyst is described. The significant advantages of this strategy include the use of cheap and easy-to-handle solid alkyne source as a surrogate of inflammable and explosive gaseous acetylene, inexpensive catalyst, wide scope of substrates, simple manipulations, and simple work-up procedures.

引用

页数：5

共 50 条

[31] Peptide ligation through copper-catalyzed formation of [1,2,3]-triazoles
Doll, Christian
Eichler, Jutta
Peptides 2004, Proceedings: BRIDGES BETWEEN DISCIPLINES, 2005, : 210 - 211
[32] Synthesis of Functionalized Isoquinolin-1(2H)-ones by Copper-Catalyzed -Arylation of Ketones with 2-Halobenzamides
Shi, Yan
Zhu, Xuebin
Mao, Haibin
Hu, Hongwen
Zhu, Chengjian
Cheng, Yixiang
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (35) : 11553 - 11557
[33] Copper-Catalyzed Direct C-3 Benzylation of Quinoxalin-2(1H)-ones with Methylarenes under Microwave Irradiation
Hu, Leqian
Yuan, Jinwei
Fu, Junhao
Zhang, Taotao
Gao, Lele
Xiao, Yongmei
Mao, Pu
Qu, Lingbo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4113 - 4120
[34] Copper-catalyzed cyclopropanation of 1,2,3,4-tetrahydropyridin-2-ones with diazoacetates - A facile and stereoselective synthesis of 3-oxo-2-azabicyclo [4.1.0] heptanes
Jain, SL
Sain, B
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 212 (1-2) : 91 - 98
[35] Copper-catalyzed chemoselective C-H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol
Su, Hai-Yan
Zhu, Xiao-Lei
Huang, Yangen
Xu, Xiu-Hua
Qing, Feng-Ling
CHEMICAL COMMUNICATIONS, 2020, 56 (84) : 12805 - 12808
[36] Copper-Catalyzed Direct Carbamoylation of Quinoxalin-2(1H)-ones with Hydrazinecarboxamides Under Mild Conditions
Chu, Xianglong
Wu, Yujuan
Lu, Haigen
Yang, Bingchuan
Ma, Chen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (09) : 1141 - 1144
[37] Copper-Catalyzed Lactamization of (E)-2-(2-Bromophenyl)-3-arylacrylamides for the Synthesis of (E)-3-Arylideneindolin-2-ones
Luo, Xiang
Zhang, Qianzhong
Jiang, Yi
Wang, Chengxin
Song, Xianheng
Li, Jianheng
Yan, Qinfang
Chan, Albert S. C.
Zou, Yong
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (09): : 6698 - 6710
[38] Copper-Catalyzed One-Pot Synthesis of 1,3,4-Oxadiazol-2(3H)-ones using DMF as the Carbonyl Source
Jiang, Ping
Su, Qin
Ablajan, Keyume
Khan, Shahid Ali
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (27)
[39] Copper-Catalyzed C(sp 3 )-H Azidation of 1,3-Dihydro-2 H -indol-2-ones Under Mild Conditions
Bao, Wen-Hui
Gao, Le-Han
Ying, Wei-Wei
Chen, Wei-Ting
Chen, Gan-Ping
Wei, Wen-Ting
Liu, Yan-Yun
Li, Qiang
SYNLETT, 2019, 30 (01) : 109 - 113
[40] Copper-Catalyzed Synthesis of Pentasubstituted Pyridines from N-Sulfonyl Ketenimines, 1,1,3,3-Tetramethylguanidine, and Acetylene Dicarboxylates
Yavari, Issa
Sheikhi, Azam
Nematpour, Manijeh
Taheri, Zohreh
HELVETICA CHIMICA ACTA, 2015, 98 (04) : 534 - 538

← 1 2 3 4 5 →