Literature DB >> 28804992

Gold-Catalyzed [4+2] Annulation/Cyclization Cascades of Benzisoxazoles with Propiolate Derivatives to Access Highly Oxygenated Tetrahydroquinolines.

Rajkumar Lalji Sahani1, Rai-Shung Liu1.   

Abstract

This work describes gold-catalyzed annulations of electron-deficient alkynes with benzisoxazoles to yield quinoline oxides chemoselectively. Chemical functionalizations of these resulting azacyclic compounds afforded various oxygenated tetrahydroquinolines which are present as the cores of many bioactive molecules. With the same reactants, a new relay catalysis using gold and zinc(II) catalysts affords highly oxygenated tetrahydroquinoline derivatives stereoselectively.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulations; gold; heterocycles; silver; synthetic methods

Year:  2017        PMID： 28804992     DOI： 10.1002/anie.201707423

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


  10 in total

1.  Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Authors:  Peter E Simm; Prakash Sekar; Jeffery Richardson; Paul W Davies
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.084

2.  An efficient 3-acylquinoline synthesis from acetophenones and anthranil via C(sp3)-H bond activation mediated by Selectfluor.

Authors:  Yejun Gao; Robert C Hider; Yongmin Ma
Journal:  RSC Adv       Date:  2019-04-02       Impact factor: 3.361

3.  Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations.

Authors:  Sovan Sundar Giri; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

4.  Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement.

Authors:  RahulKumar Rajmani Singh; Manisha Skaria; Liang-Yu Chen; Mu-Jeng Cheng; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-11-12       Impact factor: 9.825

5.  Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate.

Authors:  Antony Sekar Kulandai Raj; Kuo-Chen Tan; Liang-Yu Chen; Mu-Jeng Cheng; Rai-Shung Liu
Journal:  Chem Sci       Date:  2019-05-22       Impact factor: 9.825

6.  Practical synthesis of 3-aryl anthranils via an electrophilic aromatic substitution strategy.

Authors:  Yang Gao; Simin Yang; Minwei She; Jianhong Nie; Yanping Huo; Qian Chen; Xianwei Li; Xiao-Qiang Hu
Journal:  Chem Sci       Date:  2022-01-27       Impact factor: 9.825

7.  Dichotomy of platinum(II) and gold(III) carbene intermediates switching from N- to O-selectivity.

Authors:  Hongming Jin; Wen-Yan Tong; Jing Zhang; Matthias Rudolph; Frank Rominger; Xu Shen; Shuanglin Qu; A Stephen K Hashmi
Journal:  Nat Commun       Date:  2022-03-30       Impact factor: 14.919

8.  A high-activity cobalt-based MOF catalyst for [2 + 2 + 2] cycloaddition of diynes and alkynes: insights into alkyne affinity and selectivity control.

Authors:  Fen Xu; Xiao-Ju Si; Xiao-Ning Wang; Hao-Dong Kou; Di-Ming Chen; Chun-Sen Liu; Miao Du
Journal:  RSC Adv       Date:  2018-01-29       Impact factor: 3.361

9.  Aromatic alkyne insertion into six-membered cyclometalated pyridine complexes of iridium: different insertion modes and structurally novel products.

Authors:  Xiaodan Chu; Shaowei Zhang; Zhuo Wang; Tongyu Li; Bolin Zhu
Journal:  RSC Adv       Date:  2018-02-14       Impact factor: 3.361

10.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336
  10 in total

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