Literature DB >> 11277782

Nonconventional carbon additions to azomethines. aryl amination/indoline synthesis by direct aryl radical addition to azomethine nitrogen.

J N Johnston1, M A Plotkin, R Viswanathan, E N Prabhakaran.   

Abstract

[reaction: see text]. The generality of a new method for aryl amination has been defined. Ketimines derived from o-bromophenethylamine cyclize to the N-substituted indoline when treated with nBu3SnH and a radical initiator. The pH-neutral conditions tolerate base- and acid-sensitive functionality. The observed regioselectivity is nonconventional for addition reactions involving carbon radicals and carbon-heteroatom pi-bonds.

Entities:  

Year:  2001        PMID： 11277782

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors:  Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

2.  Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.

Authors:  Hua Yang; Rich G Carter
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

3.  Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light.

Authors:  Clarice A D Caiuby; Akbar Ali; Vinicius T Santana; Francisco W de S Lucas; Marilia S Santos; Arlene G Corrêa; Otaciro R Nascimento; Hao Jiang; Márcio W Paixão
Journal:  RSC Adv       Date:  2018-04-05       Impact factor: 4.036

4.  Total synthesis of the lycopodium alkaloid (+)-serratezomine A.

Authors:  Aroop Chandra; Julie A Pigza; Jeong-Seok Han; Daniel Mutnick; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2009-03-18       Impact factor: 15.419

5.  Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G.

Authors:  Aroop Chandra; Rajesh Viswanathan; Jeffrey N Johnston
Journal:  Org Lett       Date:  2007-11-02       Impact factor: 6.005

6.  Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure.

Authors:  Yang Liu; Li-Jie Cheng; Hai-Tao Yue; Wen Che; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-04-12       Impact factor: 9.825

7.  Free radical-mediated aryl amination: convergent two- and three-component couplings to chiral 2,3-disubstituted indolines.

Authors:  Rajesh Viswanathan; Colin R Smith; Erode N Prabhakaran; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2008-03-20       Impact factor: 4.198
  7 in total

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