Literature DB >> 22050791

Iodine-mediated cascade cyclization of enediynes to iodinated benzo[a]carbazoles.

Chin-Chau Chen1, Shyh-Chyun Yang, Ming-Jung Wu.   

Abstract

Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH(2)Cl(2) gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.

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Year:  2011        PMID： 22050791     DOI： 10.1021/jo201795t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  Green Synthesis of Halogenated Thiophenes, Selenophenes and Benzo[b]selenophenes Using Sodium Halides as a Source of Electrophilic Halogens.

Authors:  Tanay Kesharwani; Krystal A Giraudy; Jordan L Morgan; Cory Kornman; Abayomi D Olaitan
Journal:  Tetrahedron Lett       Date:  2017-01-07       Impact factor: 2.415

2.  Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Authors:  Nikki A Cochrane; Ha Nguyen; Michel R Gagne
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

3.  Regio- and stereoselective synthesis of cyclic imidates via electrophilic cyclization of 2-(1-alkynyl)benzamides. A correction.

Authors:  Saurabh Mehta; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2012-11-15       Impact factor: 4.354

4.  An expeditious iodine-catalyzed synthesis of 3-pyrrole-substituted 2-azetidinones.

Authors:  Debasish Bandyopadhyay; Jessica Cruz; Ram N Yadav; Bimal K Banik Banik
Journal:  Molecules       Date:  2012-09-28       Impact factor: 4.411

5.  Visible Light Induced Metal-Free Carbene N-Carbazolation.

Authors:  Claire Empel; Frederic W Patureau; Rene M Koenigs
Journal:  J Org Chem       Date:  2019-08-15       Impact factor: 4.354
  5 in total

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