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Ruthenium-Catalyzed Synthesis of 5-Amino-1,2,3-triazole-4-carboxylates for Triazole-Based Scaffolds: Beyond the Dimroth Rearrangement

Serena Ferrini, Jay Zumbar Chandanshive, Stefano Lena, Mauro Comes Franchini, Giuseppe Giannini, Andrea Tafi and Maurizio Taddei*

*Dipartimento di Biotecnologie, Chimica e Farmacia, UniversitÓ di Siena, Via A. Moro 2, 53100 Siena, Italy, Email: maurizio.taddeiunisi.it

S. Ferrini, J. Z. Chandanshive, S. Lena, M. C. Franchini, G. Giannini, A. Tafi, M. Taddei, J. Org. Chem., 2015, 80, 2562-2572.

DOI: 10.1021/jo502577e (free Supporting Information)



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Abstract

A ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides gives protected 5-amino-1,2,3-triazole-4-carboxylic acids, which are suitable for the preparation of peptidomimetics. When aryl or alkyl azides are reacted with N-Boc-aminopropiolates or arylynamides, the cycloaddition occurs with complete regiocontrol, while N-Boc-alkyl ynamides yield a mixture of regioisomers.

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Key Words

1,2,3-Triazoles, RuAAC


ID: J42-Y2015