Literature DB >> 28702849

Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles.

Stanley N S Vasconcelos1, Evelin Fornari2, Ignez Caracelli3, Hélio A Stefani4.   

Abstract

The Ugi multicomponent reaction has been used as an important synthetic route to obtain compounds with potential biological activity. We present the rapid and efficient synthesis of [Formula: see text]-amino-1,3-dicarbonyl compounds in moderate to good yields via Ugi flow chemistry reactions performed with a continuous flow reactor. Such [Formula: see text]-amino-1,3-dicarbonyl compounds can act as precursors for the production of [Formula: see text]-amino acids via hydrolysis of the ethyl ester group as well as building blocks for the synthesis of novel compounds with the 1,2,3-triazole ring. The [Formula: see text]-amino acid derivatives of the Ugi flow chemistry reaction products were then used for dipeptide synthesis.

Entities:  

Keywords:  Click chemistry; Flow chemistry; MRC; Multicomponent reaction; Triazole; Ugi reaction

Mesh:

Substances:

Year:  2017        PMID: 28702849     DOI: 10.1007/s11030-017-9764-5

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  20 in total

1.  Click chemistry under non-classical reaction conditions.

Authors:  C Oliver Kappe; Erik Van der Eycken
Journal:  Chem Soc Rev       Date:  2009-07-27       Impact factor: 54.564

2.  The Synthesis of Stable, Complex Organocesium Tetramic Acids through the Ugi Reaction and Cesium-Carbonate-Promoted Cascades.

Authors:  Guillermo Martinez-Ariza; Muhammad Ayaz; Sue A Roberts; Walter A Rabanal-León; Ramiro Arratia-Pérez; Christopher Hulme
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-12       Impact factor: 15.336

3.  A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitor Atazanavir.

Authors:  Luciana Dalla-Vechia; Benedikt Reichart; Toma Glasnov; Leandro S M Miranda; C Oliver Kappe; Rodrigo O M A de Souza
Journal:  Org Biomol Chem       Date:  2013-10-21       Impact factor: 3.876

4.  Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions.

Authors:  Angélica de Fátima S Barreto; Otilie E Vercillo; Mike A Birkett; John C Caulfield; Ludger A Wessjohann; Carlos Kleber Z Andrade
Journal:  Org Biomol Chem       Date:  2011-06-03       Impact factor: 3.876

Review 5.  Higher-order multicomponent reactions: beyond four reactants.

Authors:  Sebastian Brauch; Sander S van Berkel; Bernhard Westermann
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

6.  Short and novel stereospecific synthesis of trisubstituted 2,5-diketopiperazines.

Authors:  Steven L Sollis
Journal:  J Org Chem       Date:  2005-06-10       Impact factor: 4.354

7.  One-step continuous flow synthesis of highly substituted pyrrole-3-carboxylic acid derivatives via in situ hydrolysis of tert-butyl esters.

Authors:  Ananda Herath; Nicholas D P Cosford
Journal:  Org Lett       Date:  2010-10-21       Impact factor: 6.005

8.  Hydrogen-free alkene reduction in continuous flow.

Authors:  Andrew S Kleinke; Timothy F Jamison
Journal:  Org Lett       Date:  2013-01-22       Impact factor: 6.005

Review 9.  Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis.

Authors:  Flavio Fanelli; Giovanna Parisi; Leonardo Degennaro; Renzo Luisi
Journal:  Beilstein J Org Chem       Date:  2017-03-14       Impact factor: 2.883

10.  Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation.

Authors:  Nida Ambreen; Ravi Kumar; Thomas Wirth
Journal:  Beilstein J Org Chem       Date:  2013-07-17       Impact factor: 2.883

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  1 in total

1.  A Mild, Fast, and Scalable Synthesis of Substituted α-Acyloxy Ketones via Multicomponent Reaction Using a Continuous Flow Approach.

Authors:  Carlos Eduardo M Salvador; Carlos Kleber Z Andrade
Journal:  Front Chem       Date:  2019-07-30       Impact factor: 5.221

  1 in total

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