Literature DB >> 26786815

Copper-Catalyzed 8-Amido Chelation-Induced Remote C-H Amination of Quinolines.

Harekrishna Sahoo1, Mallu Kesava Reddy1, Isai Ramakrishna1, Mahiuddin Baidya2.   

Abstract

A copper-catalyzed 8-amide chelation-induced remote C-H amination of quinolines has been developed. This direct amination with readily available azodicarboxylates proceeded with perfect C5-regioselectivity offering amino-substituted 8-aminoquinolines, important bioactive molecular scaffolds, in very high yields (up to 96%). A single-electron transfer (SET)-mediated mechanism with kH /kD =1.1 was proposed after trapping of the radical intermediate.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; amination; azo compounds; copper; homogeneous catalysis

Year:  2016        PMID: 26786815     DOI: 10.1002/chem.201504207

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  2 in total

1.  An efficient nickel/silver co-catalyzed remote C-H amination of 8-aminoquinolines with azodicarboxylates at room temperature.

Authors:  Ruinan Zhao; Yaocheng Yang; Xia Wang; Peng Ren; Qian Zhang; Dong Li
Journal:  RSC Adv       Date:  2018-11-05       Impact factor: 4.036

2.  A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines.

Authors:  Damoder Reddy Motati; Dilipkumar Uredi; E Blake Watkins
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

  2 in total

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