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Synlett 2018; 29(20): 2685-2688
DOI: 10.1055/s-0037-1610323
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,4-Disubstituted 1H-1,2,3-Triazoles from 4-(1-Adamantyl)benzyl Azide through a 1,3-Dipolar Cycloaddition Reaction

Oussama Bencheikh le Hocine
a   Department of Chemistry, Faculty of Sciences, Université des Frères Mentouri Constantine 1, Constantine 25000, Algeria   eMail: dtebbani2002@yahoo.fr
,
Dahmane Tebbani*
a   Department of Chemistry, Faculty of Sciences, Université des Frères Mentouri Constantine 1, Constantine 25000, Algeria   eMail: dtebbani2002@yahoo.fr
,
Artur M. S. Silva  *
b   QOPNA, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal   eMail: artur.silva@ua.pt
› InstitutsangabenThanks are due to the University of Aveiro and FCT/MCT (Portugal) for financial support to the QOPNA Research Unit (FCT UID/QUI/00062/2013) through national founds and, where applicable, co-finance by the FEDER, within the PT2020 Partnership Agreement, as well as to the Portuguese NMR Network. Thanks are also due to the Université des Frères Mentouri Constantine 1 for a Scholarship to O.B.H.
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Publikationsverlauf

Received: 14. Oktober 2018

Accepted after revision: 15. Oktober 2018

Publikationsdatum:
21. November 2018 (online)

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Abstract

A series of new 1,4-disubstituted 1H-1,2,3-triazole derivatives were synthesized by an efficient copper-catalyzed 1,3-dipolar cyclo­addition reaction of 4-(1-adamantyl)benzyl azide with several terminal alkynes. The copper catalyst was used to provide 1,4-disubstituted 1,2,3-triazoles regioselectively in good yields.

Key words

triazoles - 1,3-dipolar cycloaddition - copper catalysis - one-pot process - adamantylbenzyl azide - click chemistry

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610323.
  • Supporting Information
 

  • References and Notes

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  • 32 Click Synthesis of 1,2,3-Triazoles 5a–s: General Procedure Cu(OAc)2·H2O (24 mg, 0.1 equiv) and NaAsc (23 mg, 0.1 equiv) were added to a stirred solution of 4-(1-adamantyl)benzyl azide (3; 0.32 g, 1.2 mmol) and the appropriate terminal alkyne 4 (1.2 mmol) in DMF (5 mL). The mixture was then stirred for 2–3 h at r.t. until the starting material was completely consumed (TLC). Sat. brine was added to the mixture and the crude product was extracted with EtOAc (3 × 10 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography [silica gel, EtOAc–PE (1:3)].
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