1402452-27-0Relevant academic research and scientific papers
Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation to Achieve Isoquinoline Synthesis
Cui, Hong,Bai, Jinku,Ai, Tianyu,Zhan, Ye,Li, Guanzhong,Rao, Honghua
supporting information, p. 4023 - 4028 (2021/05/26)
We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.
Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides
Jiang, Huanfeng,Nie, Biao,Ren, Qingyun,Wu, Wanqing,Zeng, Wei,Zhang, Ji,Zhang, Yingjun
supporting information, (2020/02/25)
A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).
Bidentate Directing-Enabled, Traceless Heterocycle Synthesis: Cobalt-Catalyzed Access to Isoquinolines
Zhou, Shuguang,Wang, Mingyang,Wang, Lili,Chen, Kehao,Wang, Jinhu,Song, Chao,Zhu, Jin
, p. 5632 - 5635 (2016/11/17)
Traceless heterocycle synthesis based on transition-metal-catalyzed C-H functionalization is synthetically appealing but has been realized only in monodentate directing systems. Bidentate directing systems allow for the achievement of high catalytic reactivity without the need for a high-cost privileged ligand. The first bidentate directing-enabled, traceless heterocycle synthesis is demonstrated in the cobalt-catalyzed synthesis of isoquinolines via 2-hydrazinylpyridine-directed C-H coupling/cyclization with alkynes. Convenient directing group installation through a ubiquitously present ketone group allows synthetic elaboration for complex molecules.
Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines
Zhu, Zhongzhi,Tang, Xiaodong,Li, Xianwei,Wu, Wanqing,Deng, Guohua,Jiang, Huanfeng
, p. 1401 - 1409 (2016/03/01)
An efficient strategy for synthesis of isoquinolines via Pd(II)-catalyzed cyclization reaction of oximes with vinyl azides or homocoupling of oximes is reported. Oximes could serve as a directing group and an internal oxidant in the transformation. This reaction features good functional group tolerance and provides a useful protocol for the synthesis of different kinds of isoquinolines under mild conditions. Some control experiments and 15N isotope labeling experiments were conducted for the mechanistic research. (Chemical Equation Presented).
Preparation of 1-methyl-3-phenylisoquinoline derivatives from oximes using polyphosphoric esters
Niemczak, Micha?,Czerniak, Kamil,Kopczyński, Tomasz
, p. 1868 - 1873 (2015/03/18)
We show a beneficial new approach to the preparation of 1-methyl-3-phenylisoquinoline derivatives. This method involves heating polyphosphate ester and the appropriate oximes obtained from 3,4-diphenylbut-3-en-2-one derivatives. The isoquinolines were syn
Palladium-catalyzed C-H oxidation of isoquinoline N-oxides: Selective alkylation with dialkyl sulfoxides and halogenation with dihalo sulfoxides
Yao, Bo,Song, Ren-Jie,Liu, Yan,Xie, Ye-Xiang,Li, Jin-Heng,Wang, Meng-Ke,Tang, Ri-Yuan,Zhang, Xing-Guo,Deng, Chen-Liang
, p. 1890 - 1896 (2012/09/22)
A novel palladium-catalyzed C-H oxidation of isoquinoline N-oxides has been developed for regioselectively synthesizing substituted isoquinolines. The method represents the first example of using dialkyl sulfoxides as the alkyl sources for the construction of 1-alkylated isoquinolines. Moreover, the regioselective halogenation of isoquinoline N-oxides is also successful using dihalo sulfoxides as the halide sources. Copyright
