Click Chemistry with 2-Ethynyl-4,5,6,7-tetrahydroindoles: Towards Functionalized Tetrahydroindole-Triazole Ensembles

Lyubov N. Sobenina; Denis N. Tomilin; Igor A. Ushakov; Albina I. Mikhaleva; J. Sh. Ma; G. Yang; Boris A. Trofimov

doi:10.1055/s-0032-1318149

Synthesis, Table of Contents

Synthesis 2013; 45(5): 678-682
DOI: 10.1055/s-0032-1318149

paper

Click Chemistry with 2-Ethynyl-4,5,6,7-tetrahydroindoles: Towards Functionalized Tetrahydroindole-Triazole Ensembles

Lyubov N. Sobenina

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Denis N. Tomilin

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Igor A. Ushakov

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Albina I. Mikhaleva

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

J. Sh. Ma

^bBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

G. Yang

^bBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

Boris A. Trofimov*

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

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Abstract

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Abstract

2-Ethynyl-4,5,6,7-tetrahydroindoles, readily available from 4,5,6,7-tetrahydroindoles and bromoacetylenes on K₂CO₃, when treated with sodium azide in DMSO, afford functionalized tetrahydroindole-triazoles ensembles. The reaction proceeds under mild conditions (room temperature) to give triazoles with acyl or ester moieties in quantitative yields.

Key words

click chemistry - cycloaddition - alkynes - sodium azide - triazoles

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References

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