51787-71-4Relevant academic research and scientific papers
Synthesis of N-(isoquinolin-1-yl)sulfonamides via Ag2O-catalyzed tandem reaction of ortho-alkynylbenzaldoximes with benchtop stabilized ketenimines
Hayatgheybi, Sepideh,Khosravi, Hormoz,Zahedian Tejeneki, Hossein,Rominger, Frank,Bijanzadeh, Hamid Reza,Balalaie, Saeed
, p. 3524 - 3529 (2021/05/10)
In this project, a moderately efficient approach to multisubstituted N-(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing ortho-alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of Ag2O, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline N-oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.
Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N -Oxide
Li, Huimin,Liao, Lihao,Zhao, Xiaodan
supporting information, p. 1688 - 1692 (2019/08/26)
An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N -oxide is developed. This transformation involves a direct intramolecular C-H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.
Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature
Sun, Jian-Guo,Zhang, Xiao-Yu,Yang, Hua,Li, Ping,Zhang, Bo
, p. 4965 - 4969 (2018/09/25)
A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl2 was employed as a precatalyst, and Et3N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.
KMnO4-mediated direct C2-selective C?H arylation of quinoline N-oxides with aromatic hydrazines
Yuan, Jin-Wei,Li, Wei-Jie,Xiao, Yong-Mei
, p. 179 - 186 (2016/12/23)
An efficient protocol for the synthesis of 2-arylquinoline N-oxides has been developed via KMnO4-mediated cross-coupling reaction of quinoline N-oxides with aromatic hydrazines in moderated to good yields. The reactions proceeded efficiently over a broad range of substrates with excellent regioselectivity and functional group tolerance.
Recent developments in the chemistry of heteroaromatic N -oxides
Wang, Youliang,Zhang, Liming
, (2015/02/19)
Selected developments in the chemistry of heteroaromatic N-oxides since 2001 are presented in this review. The use of these N-oxides, both in late-transition-metal-catalyzed oxidations of carbon-carbon triple bonds and in regioselective C-H functionalizations of the heteroarene, are contemporary topics of interest and the focus of the discussion. 1 Introduction 2 Synthesis of Heteroaromatic N-Oxides 2.1 Direct Oxidation of Hindered Heteroarenes 2.2 Through Construction of Heteroaromatic Rings 3 Heteroaromatic N-Oxides as Oxidants 3.1 Alkyne Oxidation 3.2 Allene Oxidation 3.3 Carbene Oxidation 4 Heteroaromatic N-Oxides as Substrates 4.1 Deoxygenative ortho-C-H Functionalization with Prior Activation 4.2 Deoxygenative ortho-C-H Functionalization with Nonstabilized Carbanions 4.3 Nondeoxygenative C-H Functionalization 4.3.1 ortho-C-H Functionalization 4.3.2 N-Oxide Directed ortho-Alkyl C-H Functionalization 4.3.3 N-Oxide Directed Remote C-H Functionalization 4.4 1,3-Dipolar Cycloaddition 5 Conclusion and Outlook.
Palladium-catalyzed oxidative carbamoylation of isoquinoline N-oxides with formylamides by means of dual C-H oxidative coupling
Yao, Bo,Deng, Chen-Liang,Liu, Yan,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Jin-Heng
supporting information, p. 4097 - 4100 (2015/03/18)
A new palladium-catalyzed oxidative carbamoylation reaction of isoquinoline N-oxides with formylamides for the synthesis of isoquinoline-1-carboxamides is established. The method represents the first example of the carbamoylation of isoquinoline N-oxides with formylamides to furnish arylamides using the dual C-H oxidation strategy. This journal is
Regioselective decarboxylative cross-coupling of carboxy isoquinoline N -oxides
Rouchet, Jean-Baptiste E. Y.,Schneider, Cédric,Fruit, Corinne,Hoarau, Christophe
, p. 5919 - 5927 (2015/06/16)
A straightforward method for direct decarboxylative arylation of 1- and 3-carboxy isoquinaldic acid N-oxides with aryl iodides is reported. The reaction proceeded selectively at the carboxy function site to exclusively give the corresponding C-1/sub
Synthesis of 1-aminoisoquinolines via the coinage metal cocatalyzed reaction of 2-alkynylbenzaldoximes with isocyanoacetates
Wang, Tao,Li, Rou,Yu, Danhong,Gu, Chenghao,Xiong, Fei,Chen, Zhiyuan
, p. 3213 - 3220 (2015/02/02)
An efficient reaction of 2-alkynylbenzaldoximes with 2-isocyanoacetates cocatalyzed by silver triflate and gold(I) chloride is described, providing 1-aminoisoquinolines in good to excellent yields under mild conditions. Mechanistic experiments suggest tha
Generation of 1-aroxyisoquinolines via a silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol in the presence of p-toluenesulfonyl chloride
Xiao, Qing,Zheng, Danqing,Ding, Qiuping,Wu, Jie
supporting information, p. 5119 - 5122 (2013/06/27)
A silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol promoted by p-toluenesulfonyl chloride leads to 1-aroxyisoquinolines in good yields. The presence of p-toluenesulfonyl chloride as an activator is essential for the successful transformation
AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds
Ding, Qiuping,Wang, Dan,Luo, Puying,Liu, Meiling,Pu, Shouzhi,Zhou, Liyun
supporting information, p. 1949 - 1956 (2013/10/22)
AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with various α,β-unsaturated carbonyl compounds under mild conditions are described, which provides a facile and efficient pathway for the synthesis of 1-alkylated isoquinoline derivatives. The m
