Ruthenium-catalyzed synthesis of 5-amino-1,2,3-triazole-4-carboxylates for triazole-based scaffolds: beyond the dimroth rearrangement

The Journal of Organic Chemistry
Serena FerriniMaurizio Taddei


The 5-amino-1,2,3-triazole-4-carboxylic acid is a suitable molecule for the preparation of collections of peptidomimetics or biologically active compounds based on the triazole scaffold. However, its chemistry may be influenced by the possibility of undergoing the Dimroth rearrangement. To overcome this problem, a protocol based on the ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides has been developed to give a protected version of this triazole amino acid. 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. The prepared amino acids were employed for the preparation of triazole-containing dipeptides having the structural motives typical of turn inducers. In addition, triazoles active as HSP90 inhibitors (as compound 41, IC50 = 29 nM) were synthesized.


Jan 1, 1973·Journal of the Chemical Society. Perkin Transactions 1·A Albert, H Taguchi


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Related Concepts

Carboxylic Acids
HSP90 Heat-Shock Proteins
Inhibitory Concentration 50
Cycloaddition Reaction

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