T1 and T2 – Versatile Triazene Linker Groups

Triazene as a Powerful Tool for Solid-Phase Derivatization of Phenylalanine Containing Peptides: Zygosporamide Analogues as a Proof of Concept

“…The solid-phase synthesis of zygosporamide derivatives was planned with final on-resin macrolactamization between Phe and Leu, thus being Phe the amino acid anchored to the resin through triazene linkage (Scheme ).…”

“…In particular, strategies that take advantage of the solid-phase methodology are desirable in order to implement combinatorial approaches. In this sense, anchoring of Phe through its side chain to a polymeric support via triazene provides a site for eventual derivatization of this amino acid after cleavage. Thus, the peptide cleavage from the resin affords an aromatic diazonium salt that can be easily modified.…”

Oxidation of diazenyl-protected N-heterocycles – a new entry to functionalized lactams

“…It has been shown by us [12][13][14][15][16] and others [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] that diazenylsubstituted aminestriazenescan serve as very valuable starting materials and intermediates. They are stable towards many bases, but can be cleaved under mild acidic conditions to release the free amine or amine-derivative in a simple manner.…”

Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes

“…Although this procedure has been applied often for the synthesis of arylamides, there are only few reports of triazenes, which can be seen as protected and more stable diazonium salts, being converted to amides. − The work of Satyamurthy et al encouraged us to develop a procedure for Ritter-type reactions on solid phases allowing the use of triazene linkers as protected aryl diazonium species. For a long time, our group has been working on the immobilization, modification, and cleavage of triazene linkers for solid-phase organic synthesis (SPOS), − but a Ritter-type arylamide formation was not reported by us and, to the best of our knowledge, has not been reported by others on solid supports before. As the establishment of new reactions on SPOS allows the potential use of these procedures for combinatorial chemistry and high-throughput experiments, the implementation of a Ritter-type cleavage may facilitate the access to new arylamide derivatives with improved properties.…”