Concise Synthesis of Tetrazole Macrocycle

Published on 2017-09-13T14:16:46Z (GMT) by
A concise two step synthesis of tetrazole containing macrocycles from readily accessible starting materials is presented. The first step comprises a chemoselective amidation of amino acid derived isocyanocarboxylicacid esters with unprotected symmetrical diamines to afford diverse α-isocyano-ω-amines. In the second step, the α-isocyano-ω-amines undergo an Ugi tetrazole reaction to close the macrocycle. Advantageously, this strategy allows short access to 11–19-membered macrocycles in which substituents can be independently varied at three different positions.

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Abdelraheem, Eman M.

M.; de Haan, Michel P.; Patil, Pravin; Kurpiewska, Katarzyna; Kalinowska-Tłuścik, Justyna; Shaabani, Shabnam; Dömling, Alexander (2017): Concise Synthesis of Tetrazole Macrocycle. ACS Publications. Collection.