Literature DB >> 16050724

Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3 + 2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions.

David Amantini1, Francesco Fringuelli, Oriana Piermatti, Ferdinando Pizzo, Ennio Zunino, Luigi Vaccaro.   

Abstract

TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.

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Year:  2005        PMID: 16050724     DOI: 10.1021/jo0507845

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


  7 in total

1.  Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated NH-1,2,3-triazoles.

Authors:  J R Alexander; P V Kevorkian; J J Topczewski
Journal:  Chem Commun (Camb)       Date:  2021-05-20       Impact factor: 6.222

2.  Silver Mediated Banert Cascade with Carbon Nucleophiles.

Authors:  Juliana R Alexander; Paul V Kevorkian; Joseph J Topczewski
Journal:  Org Lett       Date:  2021-04-02       Impact factor: 6.005

3.  Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.

Authors:  Matthias Wünsch; David Schröder; Tanja Fröhr; Lisa Teichmann; Sebastian Hedwig; Nils Janson; Clara Belu; Jasmin Simon; Shari Heidemeyer; Philipp Holtkamp; Jens Rudlof; Lennard Klemme; Alessa Hinzmann; Beate Neumann; Hans-Georg Stammler; Norbert Sewald
Journal:  Beilstein J Org Chem       Date:  2017-11-15       Impact factor: 2.883

4.  Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?

Authors:  Radomir Jasiński; Karolina Kula; Agnieszka Kącka; Barbara Mirosław
Journal:  Monatsh Chem       Date:  2017-03-22       Impact factor: 1.451

5.  Reactivity of ruthenium vinylidene complexes containing indenyl/dppe ligands and unsaturated bonds at Cδ with trimethylsilyl azide.

Authors:  Hui-Ling Sung; Tze-Min Her; Wen-Hsien Su; Chin-Pao Cheng
Journal:  Molecules       Date:  2012-07-17       Impact factor: 4.411

6.  A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids.

Authors:  Vera Lúcia Patrocinio Pereira; André Luiz da Silva Moura; Daniel Pais Pires Vieira; Leandro Lara de Carvalho; Eliz Regina Bueno Torres; Jeronimo da Silva Costa
Journal:  Beilstein J Org Chem       Date:  2013-04-30       Impact factor: 2.883

Review 7.  Click-chemistry approaches to π-conjugated polymers for organic electronics applications.

Authors:  Assunta Marrocchi; Antonio Facchetti; Daniela Lanari; Stefano Santoro; Luigi Vaccaro
Journal:  Chem Sci       Date:  2016-06-27       Impact factor: 9.825

  7 in total

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