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  1. Article: Synthesis of a library of glucal-derived triazoles via copper-catalyzed azide–alkyne cyclization

    Shamim, Anwar / Frederico B. Souza / Hélio A. Stefani / Stanley N.S. Vasconcelos

    Tetrahedron letters. 2017 Mar. 01, v. 58

    2017  

    Abstract: A library of glucal-derived triazoles have been synthesized using the copper-catalyzed azide-alkyne cyclization reaction starting from 3,4,6-tri-O-acetyl-d-glucal. Different trimethylsilyl substituted alkyne derivatives of glucal were first synthesized ... ...

    Abstract A library of glucal-derived triazoles have been synthesized using the copper-catalyzed azide-alkyne cyclization reaction starting from 3,4,6-tri-O-acetyl-d-glucal. Different trimethylsilyl substituted alkyne derivatives of glucal were first synthesized from 3,4,6-tri-O-acetyl-d-glucal, using Sonogashira coupling, hydrostannation and iodination steps. These glucal-based trimethylsilyl-protected alkynes were then used in the copper-catalyzed cyclization reactions with different organic azides to synthesize the corresponding triazole derivatives of d-glucal.
    Keywords alkynes ; azides ; catalysts ; chemical structure ; copper ; iodination ; triazoles
    Language English
    Dates of publication 2017-0301
    Size p. 884-888.
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2017.01.059
    Database NAL-Catalogue (AGRICOLA)

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  2. Article: Three-component reaction for the synthesis of diverse β-unsaturated α-amino esters

    Stefani, Hélio A / Ariane C.S. Sousa / Flávia Manarin / Frederico B. Souza / Witor Ribeiro Ferraz

    Tetrahedron. 2014 May 20, v. 70

    2014  

    Abstract: We describe an efficient multicomponent reaction for the preparation of β-unsaturated α-amino esters by ytterbium triflate catalyzed reaction of potassium organotrifluoroborate salts, aniline and ethyl glyoxalate. The synthetic viability of this ... ...

    Abstract We describe an efficient multicomponent reaction for the preparation of β-unsaturated α-amino esters by ytterbium triflate catalyzed reaction of potassium organotrifluoroborate salts, aniline and ethyl glyoxalate. The synthetic viability of this protocol was demonstrated by moderate to high yields, short reaction time ranging from 0.5 to 12 h, and efficiency with respect to substrate scope.
    Keywords aniline ; chemical reactions ; chemical structure ; esters ; salts
    Language English
    Dates of publication 2014-0520
    Size p. 3243-3248.
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204285-x
    ISSN 1464-5416 ; 0040-4020 ; 0563-2064
    ISSN (online) 1464-5416
    ISSN 0040-4020 ; 0563-2064
    DOI 10.1016/j.tet.2013.11.107
    Database NAL-Catalogue (AGRICOLA)

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