20359-10-8Relevant academic research and scientific papers
Synthesis of N-Heterocycles by Reductive Cyclization of Nitroalkenes Using Molybdenum Hexacarbonyl as Carbon Monoxide Surrogate
Su, Zhiyou,Liu, Bo,Liao, Hongze,Lin, Hou-Wen
, p. 4059 - 4066 (2020/06/21)
The development of a method that uses molybdenum hexacarbonyl [Mo(CO)6] as carbon monoxide (CO) surrogate for the palladium-catalyzed reductive cyclization of nitroalkenes into indoles or thienopyrroles is reported. Several types of nitroalkenes could be transformed into the desired products in excellent yields and in most cases with complete regioselectivities and higher yields than those previously reported with palladium/CO system.
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.
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
supporting information, p. 2241 - 2245 (2016/10/11)
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.
Transition metal-free Minisci reaction promoted by NCS, and TBHP: Acylation of heteroarenes
Siddaraju, Yogesh,Prabhu, Kandikere Ramaiah
supporting information, p. 959 - 967 (2016/02/03)
A method for acylation for heteroarenes under metal-free conditions has been described using NCS as an additive and TBHP as an oxidant. This method has been successfully employed in acylation of a variety of aldehyde with heteroarenes. The application of the method has been illustrated in synthesizing isoquinoline derived natural products. This strategy provides an efficient, mild and inexpensive method for acylation of heteroarenes.
A transition metal-free Minisci reaction: Acylation of isoquinolines, quinolines, and quinoxaline
Siddaraju, Yogesh,Lamani, Manjunath,Prabhu, Kandikere Ramaiah
, p. 3856 - 3865 (2014/05/20)
Transition metal-free acylation of isoquinoline, quinoline, and quinoxaline derivatives has been developed employing a cross dehydrogenative coupling (CDC) reaction with aldehydes using substoichiometric amount of TBAB (tetrabutylammonium bromide, 30 mol %) and K2S2O 8 as an oxidant. This intermolecular acylation of electron-deficient heteroarenes provides an easy access and a novel acylation method of heterocyclic compounds. The application of this CDC strategy for acylation strategy has been illustrated in synthesizing isoquinoline-derived natural products.
Oxidation of 1-benzyldihydroisoquinolines or 1- benzyltetrahydroisoquinolines with dioxygen to 1-benzoylisoquinolines
Gan, Haifeng,Lu, Yunyu,Huang, Yue,Ni, Lijun,Xu, Jinyi,Yao, Hequan,Wu, Xiaoming
experimental part, p. 1320 - 1324 (2011/04/15)
An environmental-benign methodology to synthesize 1-benzoylisoquinolines from 1-benzyl-3, 4-dihydroisoquinolines or 1-benzyl-1,2,3,4- tetrahydroisoquinolines using dioxygen as an oxidant was developed. This methodology in combination with Bischler-Napieralski reaction leads to a facile synthesis of 1-benzoylisoquinolines from phenylacetic acids and phenylethanamines.
Antiplatelet activity of benzylisoquinoline derivatives oxidized by cerium(IV) ammonium nitrate
Kuo, Reen-Yen,Chang, Fang-Rong,Wu, Chin-Chun,Patnam, Ramesh,Wang, Wei-Ya,Du, Ying-Chi,Wu, Yang-Chang
, p. 2789 - 2793 (2007/10/03)
Oxidation of 1-benzyl-3,4-dihydroisoquinolines with cerium(IV) ammonium nitrate (CAN) under mild condition yielded the mixture of corresponding 1-benzylisoquinolines (b-type) and 1-benzoylisoquinolines (a- or c-type) in an equal yields. The selective oxidation products (c-type) can be prepared by using MeCN instead of MeOH. In the antiplatelet assays, four inducers were employed, including AA, Col, PAF, and Thr. In the PAF or Col induced platelet aggregation, compounds belonging to a- and b-type showed stronger inhibitory effects than aspirin.
