Literature DB >> 27015315

Synthesis of 3,3-Spiroindolines via FeCl3-Mediated Cyclization of Aryl- or Alkene-Containing 3-Substituted N-Ac Indoles.

Raj Kumar Nandi1, Régis Guillot1, Cyrille Kouklovsky1, Guillaume Vincent1.   

Abstract

We report the cyclization of 3-substituted N-acetylindoles for the straightforward synthesis of 3,3-spiroindolines via the Friedel-Crafts reaction of an appended aryl group or the formal [2 + 2] cycloaddition of an appended alkene. Our strategy involves an Umpolung of the C2═C3 bond of the indole nucleus during FeCl3-mediated hydroarylation or annulation reactions.

Entities:  

Year:  2016        PMID： 27015315     DOI： 10.1021/acs.orglett.6b00174

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


  2 in total

1.  Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity.

Authors:  Zhen Zhang; Sneha Ray; Leah Imlay; Lauren T Callaghan; Hanspeter Niederstrasser; Prema Latha Mallipeddi; Bruce A Posner; Dawn M Wetzel; Margaret A Phillips; Myles W Smith
Journal:  Chem Sci       Date:  2021-06-30       Impact factor: 9.825

2.  Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles.

Authors:  Nazarii Sabat; Weiping Zhou; Vincent Gandon; Xavier Guinchard; Guillaume Vincent
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-02       Impact factor: 16.823
  2 in total

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