Literature DB >> 22543858

An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations.

Takuya Yokosaka1, Tetsuhiro Nemoto, Yasumasa Hamada.   

Abstract

An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.

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Year:  2012        PMID： 22543858     DOI： 10.1039/c2cc31699d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  2 in total

1.  Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles.

Authors:  Takashi Go; Akane Morimatsu; Hiroaki Wasada; Genzoh Tanabe; Osamu Muraoka; Yoshiharu Sawada; Mitsuhiro Yoshimatsu
Journal:  Beilstein J Org Chem       Date:  2018-10-29       Impact factor: 2.883

Review 2.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
  2 in total

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