Literature DB >> 25367870

An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition reaction: regioselective high-yielding synthesis of fully decorated 1,2,3-triazoles.

Adluri B Shashank1, S Karthik, R Madhavachary, Dhevalapally B Ramachary.   

Abstract

An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition (OrgAKC) reaction of a variety of enolizable arylacetones and deoxybenzoins with aryl azides was developed for the synthesis of fully decorated 1,4-diaryl-5-methyl(alkyl)-1,2,3-triazoles in excellent yields with high regioselectivity at 25 °C for 0.5-6 h. This reaction has an excellent outcome with reference to reaction rate, yield, regioselectivity, operation simplicity, and availability of substrates and catalyst. This reaction has advantages over the previously known metal-mediated reactions.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  azides; click reaction; ketones; organocatalysis; triazoles

Year:  2014        PMID: 25367870     DOI: 10.1002/chem.201405501

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

1.  Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives.

Authors:  Monalisa Kundu; Ishani Bhaumik; Anup Kumar Misra
Journal:  Glycoconj J       Date:  2019-07-05       Impact factor: 2.916

2.  An Efficient Approach to Phosphorylated Isoindoline Fused with Triazoles via Zn-Catalyzed Cascade Cyclization of 2-Propynol Benzyl Azides and Diarylphosphine Oxides.

Authors:  Tao Yang; Xian-Rong Song; Ruchun Yang; Haixin Ding; Jiang Bai; Qiang Xiao
Journal:  Molecules       Date:  2019-09-29       Impact factor: 4.411

3.  Mesoionic Imines (MIIs): Strong Donors and Versatile Ligands for Transition Metals and Main Group Substrates.

Authors:  Richard Rudolf; Nicolás I Neuman; Robert R M Walter; Mark R Ringenberg; Biprajit Sarkar
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-19       Impact factor: 16.823

  3 in total

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