Literature DB >> 28961354

Oxidative Rearrangement Coupling Reaction for the Functionalization of Tetrahydro-β-carbolines with Aromatic Amines.

Jinxiang Ye1, Jianlei Wu1, Tingting Lv1, Guolin Wu1, Yu Gao1, Haijun Chen1.   

Abstract

The observation of an unexpected oxidative rearrangement coupling reaction led to the development of a novel method for the efficient functionalization of tetrahydro-β-carbolines (THβCs). The treatment of THβCs with photogenerated singlet oxygen (1 O2 ) afforded unstable dioxetanes, which underwent further transformation to form new bonds in the presence of trifluoroacetic acid. This operationally simple protocol exhibits broad functional-group tolerance and is suitable for the late-stage functionalization of complex druglike molecules.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  oxidative functionalization; rearrangement; singlet oxygen; tetrahydro-β-carbolines; visible light

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Substances：

Year:  2017        PMID： 28961354     DOI： 10.1002/anie.201708893

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  3 in total

1.  Visible-Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N-Diacyliminium Ions.

Authors:  Mario Frahm; Thorsten von Drathen; Lisa Marie Gronbach; Alice Voss; Felix Lorenz; Jonas Bresien; Alexander Villinger; Frank Hoffmann; Malte Brasholz
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-23       Impact factor: 15.336

2.  Pyrrolo [3,4-b]-quinolin-9-amine compound FZU-0038-056 suppresses triple-negative breast cancer partially through inhibiting the expression of Bcl-2.

Authors:  Danping Wang; Zhi Nie; Xiaoyan Jiang; Jinxiang Ye; Zhimin Wei; Dating Cheng; Chenyang Wang; Yingying Wu; Rong Liu; Haijun Chen; Ceshi Chen; Chunyan Wang
Journal:  Aging (Albany NY)       Date:  2020-05-23       Impact factor: 5.682

3.  TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline.

Authors:  Manda Sathish; Akash P Sakla; Fabiane M Nachtigall; Leonardo S Santos; Nagula Shankaraiah
Journal:  RSC Adv       Date:  2021-05-05       Impact factor: 4.036
  3 in total

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