Literature DB >> 19839585

Synthesis of 4- and 6-azaindoles via the Fischer reaction.

Matthieu Jeanty1, Jérôme Blu, Franck Suzenet, Gérald Guillaumet.   

Abstract

Contrary to the common idea that Fischer indole cyclization often cannot be effectively applied to the synthesis of the corresponding azaindoles, we show that this approach can be actually very efficient for the formation of 4- and 6-azaindoles bearing an electron-donating group on the starting pyridylhydrazines. Two 4-azaindole natural product analogues were synthesized in a few steps and very good overall yields.

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Year:  2009        PMID: 19839585     DOI: 10.1021/ol902139r

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


  4 in total

1.  Original Design of Fluorescent Ligands by Fusing BODIPY and Melatonin Neurohormone.

Authors:  Jérémy Thireau; Justine Marteaux; Philippe Delagrange; Francois Lefoulon; Laurence Dufourny; Gérald Guillaumet; Franck Suzenet
Journal:  ACS Med Chem Lett       Date:  2013-11-20       Impact factor: 4.345

2.  Understanding and Interrupting the Fischer Azaindolization Reaction.

Authors:  Bryan J Simmons; Marie Hoffmann; Pier Alexandre Champagne; Elias Picazo; Katsuya Yamakawa; Lucas A Morrill; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2017-10-12       Impact factor: 15.419

3.  Design and Synthesis of Novel Deuterated Ligands Functionally Selective for the γ-Aminobutyric Acid Type A Receptor (GABAAR) α6 Subtype with Improved Metabolic Stability and Enhanced Bioavailability.

Authors:  Daniel E Knutson; Revathi Kodali; Branka Divović; Marco Treven; Michael R Stephen; Nicolas M Zahn; Vladimir Dobričić; Alec T Huber; Matheus A Meirelles; Ranjit S Verma; Laurin Wimmer; Christopher Witzigmann; Leggy A Arnold; Lih-Chu Chiou; Margot Ernst; Marko D Mihovilovic; Miroslav M Savić; Werner Sieghart; James M Cook
Journal:  J Med Chem       Date:  2018-03-06       Impact factor: 8.039

4.  Marine Sponge/H3PO4: As a Naturally Occurring Chiral Catalyst for Solvent-free Fischer-Indole Synthesis.

Authors:  Mohammad Reza Shushizadeh; Azar Mostoufi; Rashid Badri; Somaye Azizyan
Journal:  Jundishapur J Nat Pharm Prod       Date:  2013-11-01
  4 in total

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