Copper-catalyzed annulation of 2-bromobenzoic esters with terminal alkynes towards 3-substituted isocoumarins

被引：17

作者：

Sun, Mengli ^{[1
]}

Su, Lebin ^{[1
]}

Dong, Jianyu ^{[1
]}

Liu, Long ^{[1
]}

Zhou, Yongbo ^{[1
]}

Yin, Shuang-Feng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 25期

关键词：

Isocoumarins; Copper catalysis; Terminal alkynes; 2-Bromobenzoic esters; O-IODOBENZOIC ACID; BENZOIC-ACIDS; REGIOSELECTIVE SYNTHESIS; ALPHA-PYRONES; OXIDATIVE CYCLIZATION; COUPLING REACTIONS; ARYL; PHTHALIDES; DERIVATIVES; BOND;

D O I：

10.1016/j.tetlet.2017.05.019

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-substituted isocoumarins that are an important class of biologically active scaffolds via annulation of 2-bromobenzoic esters with terminal alkynes by copper catalyzed is described. The advantages of this method include mild reaction conditions, high yield and regioselectivity, and wide tolerance toward functional groups. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2433 / 2437

页数：5

共 50 条

[21] Copper-Catalyzed [3+2] Annulation of Azides with a (Difluorovinyl)zinc Complex, Fluoroacetylene Equivalent
Fujita, Takeshi
Takeishi, Masafumi
Ichikawa, Junji
ORGANIC LETTERS, 2020, 22 (23) : 9253 - 9257
[22] One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes
Li, Yunlan
Zhang, Qiurui
Xu, Xuefeng
Zhang, Xu
Yang, Yurong
Yi, Wei
TETRAHEDRON LETTERS, 2019, 60 (14) : 965 - 970
[23] Copper-catalyzed annulation of heteroaromatic β-halo-α,β-unsaturated carboxylic acids with alkynes for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones
Gu, Da-Wei
Guo, Xun-Xiang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (32) : 6114 - 6120
[24] Copper-Catalyzed [4+1] Annulation between α-Hydroxy Ketones and Nitriles: An Approach to Highly Substituted 3(2H)-Furanones
He, Haitao
Qi, Chaorong
Hu, Xiaohan
Ouyang, Lu
Xiong, Wenfang
Jiang, Huanfeng
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (10) : 4957 - 4965
[25] Copper-Catalyzed Direct Alkynylation of Electron-Deficient Polyfluoroarenes with Terminal Alkynes Using O2 as an Oxidant
Wei, Ye
Zhao, Huaiqing
Kan, Jian
Su, Weiping
Hong, Maochun
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) : 2522 - +
[26] Copper-catalyzed [3+2+1] annulation of anthranils with phenylacetaldehydes: Synthesis of 8-acylquinolines
Shi, Kai
Zhu, Hao
Ren, Fei
Liu, Shuang
Song, Yingying
Li, Wei
Zou, Liang-Hua
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (06) : 1003 - 1006
[27] Synthesis of Substituted 4H-Thiochromen-4-imines via Copper-Catalyzed Cyclization Cascades of o-Bromobenzothioamides with Terminal Alkynes
Ma, Yong-Gang
Huang, Meng-Qao
Liu, Zhenhua
Liu, Jian-Quan
Wang, Xiang-Shan
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) : 9504 - 9509
[28] Ligand-free copper-catalyzed coupling of α-amino acids with N-Boc-2-iodoanilines for the synthesis of enantiopure 3-substituted dihydroquinoxalinones
Luo, Sheng
De Brabander, Jef K.
TETRAHEDRON LETTERS, 2015, 56 (23) : 3179 - 3182
[29] Copper-Catalyzed C(sp3)- Functionalization and Annulation of 2-Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N-Oxides
Patel, Chandresh K. K.
Gujjarappa, Raghuram
Kant, Kamal
Ghanta, Susanta
Singh, Virender
Kabi, Arup K. K.
Al-Zaqri, Nabil
Malakar, Chandi C. C.
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (13) : 2203 - 2210
[30] Pd(ii)-catalyzed annulation of terminal alkynes with 2-pyridinyl-substituted p-quinone methides: direct access to indolizines
Ahmad, Feroz
Ranga, Pavit K.
Pankhade, Yogesh A.
Fatma, Shaheen
Gouda, Ashrumochan
Anand, Ramasamy Vijaya
CHEMICAL COMMUNICATIONS, 2022, 58 (95) : 13238 - 13241

← 1 2 3 4 5 →