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Concise Synthesis of Tetrazole Macrocycle.

ABSTRACT: 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 ?-isocyano-?-amines. In the second step, the ?-isocyano-?-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.

SUBMITTER: Abdelraheem EMM

PROVIDER: S-EPMC5633831 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Concise Synthesis of Tetrazole Macrocycle.

Abdelraheem Eman M M EMM de Haan Michel P MP Patil Pravin P Kurpiewska Katarzyna K Kalinowska-Tłuścik Justyna J Shaabani Shabnam S Dömling Alexander A

Organic letters 20170913 19

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 subst ...[more]

PMID: 28901777

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