58021-72-0Relevant academic research and scientific papers
Transition-Metal-Free Acylation of Quinolines and Isoquinolines with Arylmethanols via Oxidative Cross-Dehydrogenative Coupling Reactions
Adib, Mehdi,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Kabiri, Roya,Gohari, Seyed Jamal Addin
, p. 2241 - 2245 (2016)
An efficient acylation of quinolines and isoquinolines is described by use of arylmethanols as the acylating agents through a C-C bond formation via an oxidative cross-dehydrogenative coupling (CDC) strategy. This C-aroylation reaction was carried out by use of K2S2O8 as oxidant and methyltrioctylammonium chloride (Aliquat 336) as a transfer agent in MeCN at 80 °C under transition-metal-free conditions.
Site-selective c-h acylation of pyridinium derivatives by photoredox catalysis
Jung, Sungwoo,Lee, Hyeonyeong,Moon, Yonghoon,Jung, Hoi-Yun,Hong, Sungwoo
, p. 9891 - 9896 (2019/10/14)
A strategy for visible-light-induced site-selective C-H acylation of pyridinium salts was developed by employing N-methoxy-or N-aminopyridinium salts, offering a powerful synthetic tool for accessing highly valuable C2- A nd C4-acylated pyridines. The met
Visible-Light-Mediated Direct Decarboxylative Acylation of Electron-Deficient Heteroarenes Using α-Ketoacids
Manna, Sabyasachi,Prabhu, Kandikere Ramaiah
, (2019/05/08)
Acylation of electron-deficient heteroaromatic compounds has been developed using visible light. α-Ketoacids have been used as an efficient source of acyl radicals under photoredox conditions. The in situ generated acyl radicals from α-ketoacids have been coupled to a wide variety of electron-deficient heteroaromatic compounds in a Minisci type reaction. This method would be attractive to access biologically attractive molecules.
Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies
Sharma, Shweta,Kumar, Mukesh,Vishwakarma, Ram A.,Verma, Mahendra K.,Singh, Parvinder Pal
, p. 12420 - 12431 (2018/10/20)
Herein, we report an original one-step, simple, room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water is a source of oxygen in the acylated product, and head space GC-MS experiment shows the C-C cleavage occurs via release as CO2.
Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
Zheng, Bo,Qu, Hui-Ya,Meng, Tian-Zhuo,Lu, Xia,Zheng, Jie,He, Yun-Gang,Fan, Qi-Qi,Shi, Xiao-Xin
, p. 28997 - 29007 (2018/08/29)
Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.
Metal-free decarboxylative acylation of isoquinolines using α-keto acids in water
Chaubey, Narendra R.,Singh, Krishna Nand
supporting information, p. 2347 - 2350 (2017/05/29)
An efficient method for acylation of isoquinolines has been developed using α-ketoacids under metal- and additive-free conditions in water. The protocol involves C(sp2)–H functionalization of isoquinolines providing an easy access to C1-benzoylated isoquinolines, which constitute the core structure of a number of biological active compounds and serve as key intermediate in the synthesis of many alkaloids.
Palladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline: N -oxides and nitroalkenes
Li, Jiu-Ling,Li, Wei-Ze,Wang, Ying-Chun,Ren, Qiu,Wang, Heng-Shan,Pan, Ying-Ming
, p. 10028 - 10031 (2016/08/15)
C1-Benzoyl isoquinolines can be generated via a palladium(ii)-catalyzed C-C and C-O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C-H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.
Method for synthesizing isoquinoline-1-aryl ketone compound
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Paragraph 0014; 0016; 0017; 0018; 0019, (2016/10/10)
The invention discloses a method for synthesizing an isoquinoline-1-aryl ketone compound. The method comprises the following steps: adding 10% of a Pd catalyst and 1-5 mL of an aprotic polar solvent into a sealed tube, stirring for 5-10 minutes at the roo
Regiospecific benzoylation of electron-deficient n -heterocycles with methylbenzenes via a minisci-type reaction
Ali, Wajid,Behera, Ahalya,Guin, Srimanta,Patel, Bhisma K.
, p. 5625 - 5632 (2015/06/16)
A regioselective cross-dehydrogenative coupling between electron-deficient N-heterocycles (isoquinoline, quinolines, and quinoxalines) and methylbenzenes leading to regiospecific C-aroylation has been accomplished using AlCl3 as the catalyst in
C1-Benzyl and benzoyl isoquinoline synthesis through direct oxidative cross-dehydrogenative coupling with methyl arenes
Wan, Miao,Lou, Hongxiang,Liu, Lei
supporting information, p. 13953 - 13956 (2015/09/07)
An oxidative cross-dehydrogenative coupling (CDC) of isoquinolines with methyl arenes has been developed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl and -benzoyl isoquinolines. The direct use of readily available methyl arenes as coupling partners avoids unproductive steps for preactivating the functional group installation, and is therefore attractive. The method exhibits excellent chemoselectivity, affording exclusive benzylated products in the presence of DTBP and a catalytic amount of Y(OTf)3, and yielding benzoylated ones with TBHP and a catalytic amount of MnO2.
