Two-Step Macrocycle Synthesis by Classical Ugi Reaction

Eman M M Abdelraheem; Samad Khaksar; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Shabnam Shaabani; Alexander Dömling

doi:10.1021/acs.joc.7b02984

Two-Step Macrocycle Synthesis by Classical Ugi Reaction

Eman M M Abdelraheem, Samad Khaksar, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Shabnam Shaabani, Alexander Dömling

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Abstract

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 one-pot procedure. This synthetic approach is short and efficient and leads to a wide range of macrocycles with different ring sizes.

Original language	English
Pages (from-to)	1441-1447
Number of pages	7
Journal	The Journal of Organic Chemistry
Volume	83
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.7b02984
Publication status	Published - 2-Feb-2018

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Journal Article

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10.1021/acs.joc.7b02984Licence: CC BY-NC-ND

Two-Step Macrocycle Synthesis by Classical Ugi ReactionFinal publisher's version, 1.73 MBLicence: CC BY-NC-ND

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CCDC 1577989: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Khaksar, S. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tuścik, J. (Contributor), Shaabani, S. (Contributor) & Dömling, A. (Contributor), University of Groningen, 3-Oct-2017
DOI: 10.5517/ccdc.csd.cc1pz0wk
Dataset
CCDC 1577990: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Khaksar, S. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tuścik, J. (Contributor), Shaabani, S. (Contributor) & Dömling, A. (Contributor), University of Groningen, 3-Oct-2017
DOI: 10.5517/ccdc.csd.cc1pz0xl
Dataset
CCDC 1577248: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Khaksar, S. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tuścik, J. (Contributor), Shaabani, S. (Contributor) & Dömling, A. (Contributor), University of Groningen, 29-Sept-2017
DOI: 10.5517/ccdc.csd.cc1py7zv
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Cite this

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title = "Two-Step Macrocycle Synthesis by Classical Ugi Reaction",

abstract = "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 one-pot procedure. This synthetic approach is short and efficient and leads to a wide range of macrocycles with different ring sizes.",

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doi = "10.1021/acs.joc.7b02984",

language = "English",

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T1 - Two-Step Macrocycle Synthesis by Classical Ugi Reaction

AU - Abdelraheem, Eman M M

AU - Khaksar, Samad

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tłuścik, Justyna

AU - Shaabani, Shabnam

AU - Dömling, Alexander

PY - 2018/2/2

Y1 - 2018/2/2

N2 - 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 one-pot procedure. This synthetic approach is short and efficient and leads to a wide range of macrocycles with different ring sizes.

AB - 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 one-pot procedure. This synthetic approach is short and efficient and leads to a wide range of macrocycles with different ring sizes.

KW - Journal Article

U2 - 10.1021/acs.joc.7b02984

DO - 10.1021/acs.joc.7b02984

M3 - Article

C2 - 29327924

SN - 0022-3263

VL - 83

SP - 1441

EP - 1447

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 3

ER -

Two-Step Macrocycle Synthesis by Classical Ugi Reaction

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CCDC 1577989: Experimental Crystal Structure Determination

CCDC 1577990: Experimental Crystal Structure Determination

CCDC 1577248: Experimental Crystal Structure Determination

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