Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

Abstract

The Cu(I)-catalyzed azide-alkyne cycloaddition reaction, also known as click chemistry, has become a useful tool for the facile formation of 1,2,3-triazoles. Specifically, the utility of this reaction has been demonstrated by the synthesis of structurally diverse bi- and bis-1,2,3-triazoles. The present review focuses on the synthesis of such bi- and bistriazoles and the importance of using copper-promoted click chemistry (CuAAC) for such transformations. In addition, the application of bitriazoles and the related CuAAAC reaction in different fields, including medicinal chemistry, coordination chemistry, biochemistry, and supramolecular chemistry, have been highlighted.

Keywords: bistriazoles; click chemistry; cycloaddition; homogeneous catalysis; oxidative coupling.

Scheme 1

The synthesis of triazoles through the Huisgen cycloaddition of azides to alkynes.

Scheme 2

The synthesis of symmetrically substituted 4,4'-bitriazoles.

Scheme 3

The synthesis of unsymmetrically substituted 4,4'-bitriazoles.

Scheme 4

The stepwise preparation of unsymmetrical 4,4'-bitriazoles.

Scheme 5

The synthesis of 5,5'-bitriazoles.

Scheme 6

The synthesis of bistriazoles and cyclic 5,5^’-bitriazoles under different catalytic systems.

Scheme 7

The double CuAAC reaction between helicenequinone and 1,1^’-diazidoferrocene.

Scheme 8

The synthesis of 1,2,3-triazoles and 5,5’-bitriazoles from acetylenic amide.

Scheme 9

The amine-functionalized polysiloxane-mediated divergent synthesis of trizaoles and bitriazoles.

Scheme 10

The cyclic BINOL-based 5,5’-bitriazoles.

Scheme 11

The one-pot click–click reactions for the synthesis of bistriazoles.

Scheme 12

The synthesis of bis(indolyl)methane-derivatized 1,2,3-bistriazoles.

Scheme 13

The sequential, chemoselective preparation of bistriazoles.

Scheme 14

The sequential SPAAC and CuAAC reaction for the preparation of bistriazoles.

Scheme 15

The synthesis of D-mannitol-based bistriazoles.

Scheme 16

The synthesis of ester-linked and amide-linked bistriazoles.

Scheme 17

The synthesis of acenothiadiazole-based bistriazoles.

Scheme 18

The pyrene-appended thiacalix[4]arene-based bistriazole.

Scheme 19

The synthesis of triazole-based tetradentate ligands.

Scheme 20

The synthesis of phenanthroline-2,9-bistriazoles.

Scheme 21

The three-component reaction for the synthesis of bistriazoles.

Scheme 22

The one-pot synthesis of bistriazoles.

Scheme 23

The synthesis of polymer-bearing 1,2,3-bistriazole.

Scheme 24

The synthesis of bistriazoles via a sequential one-pot reaction.