3 years ago

Concise Synthesis of Tetrazole Macrocycle

Concise Synthesis of Tetrazole Macrocycle
Pravin Patil, Eman M. M. Abdelraheem, Shabnam Shaabani, Justyna Kalinowska-Tłuścik, Alexander Dömling, Michel P. de Haan, Katarzyna Kurpiewska
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02319

DOI: 10.1021/acs.orglett.7b02319

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