Concise Synthesis of Tetrazole Macrocycle

Eman M M Abdelraheem; Michel P de Haan; Pravin Patil; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Shabnam Shaabani; Alexander Dömling

doi:10.1021/acs.orglett.7b02319

Concise Synthesis of Tetrazole Macrocycle

Eman M M Abdelraheem, Michel P de Haan, Pravin Patil, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Shabnam Shaabani, Alexander Dömling

Onderzoeksoutput › Academic › peer review

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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.

Originele taal-2	English
Pagina's (van-tot)	5078-5081
Aantal pagina's	4
Tijdschrift	Organic letters
Volume	19
DOI's	https://doi.org/10.1021/acs.orglett.7b02319
Status	Published - 13-sep.-2017

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10.1021/acs.orglett.7b02319Licentie: CC BY-NC-ND

Concise Synthesis of Tetrazole MacrocycleFinal publisher's version, 1,38 MBLicentie: CC BY-NC-ND

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CCDC 1548701: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Haan , de, M. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor), Shaabani, S. (Contributor) & Dömling, A. (Contributor), University of Groningen, 8-mei-2017
DOI: 10.5517/ccdc.csd.cc1nzk39
Dataset
CCDC 1548704: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Haan , de, M. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor), Shaabani, S. (Contributor) & Dömling, A. (Contributor), University of Groningen, 8-mei-2017
DOI: 10.5517/ccdc.csd.cc1nzk6d
Dataset

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title = "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 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.",

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author = "Abdelraheem, {Eman M M} and {de Haan}, {Michel P} and Pravin Patil and Katarzyna Kurpiewska and Justyna Kalinowska-T{\l}u{\'s}cik and Shabnam Shaabani and Alexander D{\"o}mling",

year = "2017",

month = sep,

day = "13",

doi = "10.1021/acs.orglett.7b02319",

language = "English",

volume = "19",

pages = "5078--5081",

journal = "Org.Lett.",

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T1 - Concise Synthesis of Tetrazole Macrocycle

AU - Abdelraheem, Eman M M

AU - de Haan, Michel P

AU - Patil, Pravin

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tłuścik, Justyna

AU - Shaabani, Shabnam

AU - Dömling, Alexander

PY - 2017/9/13

Y1 - 2017/9/13

N2 - 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.

AB - 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.

KW - Journal Article

KW - PROTEIN DRUGGABILITY

KW - UGI REACTION

KW - TARGETS

KW - PEPTIDOMIMETICS

KW - MOLECULES

KW - PEPTIDES

KW - DRUGS

KW - BIND

KW - RULE

U2 - 10.1021/acs.orglett.7b02319

DO - 10.1021/acs.orglett.7b02319

M3 - Article

C2 - 28901777

VL - 19

SP - 5078

EP - 5081

JO - Org.Lett.

JF - Org.Lett.

SN - 1523-7060

ER -

Concise Synthesis of Tetrazole Macrocycle

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Datasets

CCDC 1548701: Experimental Crystal Structure Determination

CCDC 1548704: Experimental Crystal Structure Determination

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