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Two-Step Macrocycle Synthesis by Classical Ugi Reaction.

ABSTRACT: The direct nonpeptidic macrocycle synthesis of ?-isocyano-?-amines via the classical Ugi four-component reaction (U-4CR) is introduced. Herein an efficient and flexible two-step procedure to complex macrocycles is reported. In the first step, the reaction between unprotected diamines and isocyanocarboxylic acids gives high diversity of unprecedented building blocks in high yield. In the next step, the ?-isocyano-?-amines undergo a U-4CR with high diversity of aldehydes and carboxylic acids in a one-pot procedure. This synthetic approach is short and efficient and leads to a wide range of macrocycles with different ring sizes.

SUBMITTER: Abdelraheem EMM

PROVIDER: S-EPMC5799868 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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Two-Step Macrocycle Synthesis by Classical Ugi Reaction.

Abdelraheem Eman M M EMM Khaksar Samad S Kurpiewska Katarzyna K Kalinowska-Tłuścik Justyna J Shaabani Shabnam S Dömling Alexander A

The Journal of organic chemistry 20180124 3

The direct nonpeptidic macrocycle synthesis of α-isocyano-ω-amines via the classical Ugi four-component reaction (U-4CR) is introduced. Herein an efficient and flexible two-step procedure to complex macrocycles is reported. In the first step, the reaction between unprotected diamines and isocyanocarboxylic acids gives high diversity of unprecedented building blocks in high yield. In the next step, the α-isocyano-ω-amines undergo a U-4CR with high diversity of aldehydes and carboxylic acids in a ...[more]

PMID: 29327924

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