2016•Organic LettersOpen access

Cleavable β-Cyanoethyl Isocyanide in the Ugi Tetrazole Reaction

Edwin Kroon, Katarzyna Kurpiewska, Justyna Kalinowska‐Tłuścik, Alexander S. S. Dömling

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Abstract

β-Cyanoethyl isocyanide is introduced as a cleavable isocyanide in the Ugi tetrazole reaction. Eleven examples are described that exhibit a broad scope and are obtained in good overall yields. The obtained 1H-tetrazole scaffold is an important bioisostere for carboxylic acids, and the method described here is a valuable alternative route to known procedures.

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What this paper is about

β-Cyanoethyl isocyanide is introduced as a cleavable isocyanide in the Ugi tetrazole reaction. Eleven examples are described that exhibit a broad scope and are obtained in good overall yields. The obtained 1H-tetrazole scaffold is an important bioisostere for carboxylic acids, and the method described here is a valuable alternative route to known procedures.

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Available abstract

β-Cyanoethyl isocyanide is introduced as a cleavable isocyanide in the Ugi tetrazole reaction. Eleven examples are described that exhibit a broad scope and are obtained in good overall yields. The obtained 1H-tetrazole scaffold is an important bioisostere for carboxylic acids, and the method described here is a valuable alternative route to known procedures.

Key concepts: Isocyanide, Tetrazole, Bioisostere, Chemistry, Ugi reaction, Combinatorial chemistry, Scope (computer science), Organic chemistry

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