Issue 30, 2022
From the journal:

Organic & Biomolecular Chemistry

Modular synthesis of triazoles from 2-azidoacrylamides having a nucleophilic amino group†

Hinano Takemura,a   Gaku Orimoto,b   Akihiro Kobayashi,ab   Takamitsu Hosoya ORCID logo a  and  Suguru Yoshida ORCID logo *b  

* Corresponding authors

a Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

b Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan
E-mail: s-yoshida@rs.tus.ac.jp

Abstract

Assembling methods using 2-azidoacrylamides having a nucleophilic amino group are disclosed. Divergent transformations of the amine-type trivalent platform were accomplished with a wide variety of electrophiles to obtain a broad range of 2-azidoacrylamides involving a fluorosulfonyl group-containing trivalent platform. Consecutive click conjugations including triazole formation, thiol–ene-type 1,4-addition, and SuFEx reactions realized the efficient assembly of easily available simple modules.

Graphical abstract: Modular synthesis of triazoles from 2-azidoacrylamides having a nucleophilic amino group

  • This article is part of the themed collection: New Talent
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Article information

DOI
https://doi.org/10.1039/D2OB00151A
Article type
Paper
Submitted
24 Jan 2022
Accepted
15 Feb 2022
First published
15 Feb 2022
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2022,20, 6007-6011

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Modular synthesis of triazoles from 2-azidoacrylamides having a nucleophilic amino group

H. Takemura, G. Orimoto, A. Kobayashi, T. Hosoya and S. Yoshida, Org. Biomol. Chem., 2022, 20, 6007 DOI: 10.1039/D2OB00151A

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