Concise Synthesis of Tetrazole-Ketopiperazines by Two Consecutive Ugi Reactions

Tryfon Zarganes-Tzitzikas; Pravin Patil; Kareem Khoury; Eberhardt Herdtweck; Alex Dömling

doi:10.1002/ejoc.201403401

Concise Synthesis of Tetrazole-Ketopiperazines by Two Consecutive Ugi Reactions

Tryfon Zarganes-Tzitzikas
, Pravin Patil
, Kareem Khoury
, Eberhardt Herdtweck
, Alex Dömling^*

^*Corresponding author for this work

Drug Design

Research output: Contribution to journal › Article › Academic › peer-review

38 Citations (Scopus)

102 Downloads (Pure)

Abstract

A concise route for the synthesis of the novel compound class tetrazole-diketopiperazines was developed. The approach involves the use of two multicomponent reactions: the Ugi tetrazole four-component reaction (4CR) and the classical intramolecular Ugi 4CR. The tetrazole-diketopiperazines comprise analogs of and are bioisosteric to bioactive diketopiperazines, which thus draws attention for novel bioactive compound design. This scaffold was produced to fill the screening deck of the European lead factory.

Original language	English
Pages (from-to)	51-55
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201403401
Publication status	Published - Jan-2015

Keywords

Multicomponent reactions
Nitrogen heterocycles
Ketopiperazines
Screening library
Isocyanides
COMBINATORIAL LIBRARIES
SOLID-PHASE
DIKETOPIPERAZINES
DERIVATIVES
ISONITRILEN
CHEMISTRY
SURROGATE
RING
ZINC

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10.1002/ejoc.201403401

Concise Synthesis of Tetrazole-Ketopiperazines by Two Consecutive Ugi ReactionsFinal publisher's version, 4.1 MBLicence: Taverne

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38 Citations
2 Digital or Visual Products

CCDC 986844: Experimental Crystal Structure Determination
Zarganes-Tzitzikas, T., Patil, P., Khoury, K., Herdtweck, E. & Dömling, A., 2015
Research output: Non-textual form › Digital or Visual Products › Academic
CCDC 986845: Experimental Crystal Structure Determination
Zarganes-Tzitzikas, T., Patil, P., Khoury, K., Herdtweck, E. & Dömling, A., 2015
Research output: Non-textual form › Digital or Visual Products › Academic

CCDC 986844: Experimental Crystal Structure Determination
Zarganis Tzitzikas, T. (Contributor), Patil, P. (Contributor), Khoury, K. (Contributor), Herdtweck, E. (Contributor) & Dömling, A. (Contributor), University of Groningen, 22-Jan-2015
DOI: 10.5517/cc123wpr
Dataset
CCDC 986845: Experimental Crystal Structure Determination
Zarganis Tzitzikas, T. (Contributor), Patil, P. (Contributor), Khoury, K. (Contributor), Herdtweck, E. (Contributor) & Dömling, A. (Contributor), University of Groningen, 22-Jan-2015
DOI: 10.5517/cc123wqs
Dataset

Cite this

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title = "Concise Synthesis of Tetrazole-Ketopiperazines by Two Consecutive Ugi Reactions",

abstract = "A concise route for the synthesis of the novel compound class tetrazole-diketopiperazines was developed. The approach involves the use of two multicomponent reactions: the Ugi tetrazole four-component reaction (4CR) and the classical intramolecular Ugi 4CR. The tetrazole-diketopiperazines comprise analogs of and are bioisosteric to bioactive diketopiperazines, which thus draws attention for novel bioactive compound design. This scaffold was produced to fill the screening deck of the European lead factory.",

keywords = "Multicomponent reactions, Nitrogen heterocycles, Ketopiperazines, Screening library, Isocyanides, COMBINATORIAL LIBRARIES, SOLID-PHASE, DIKETOPIPERAZINES, DERIVATIVES, ISONITRILEN, CHEMISTRY, SURROGATE, RING, ZINC",

author = "Tryfon Zarganes-Tzitzikas and Pravin Patil and Kareem Khoury and Eberhardt Herdtweck and Alex D{\"o}mling",

year = "2015",

month = jan,

doi = "10.1002/ejoc.201403401",

language = "English",

volume = "2015",

pages = "51--55",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "1",

}

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T1 - Concise Synthesis of Tetrazole-Ketopiperazines by Two Consecutive Ugi Reactions

AU - Zarganes-Tzitzikas, Tryfon

AU - Patil, Pravin

AU - Khoury, Kareem

AU - Herdtweck, Eberhardt

AU - Dömling, Alex

PY - 2015/1

Y1 - 2015/1

N2 - A concise route for the synthesis of the novel compound class tetrazole-diketopiperazines was developed. The approach involves the use of two multicomponent reactions: the Ugi tetrazole four-component reaction (4CR) and the classical intramolecular Ugi 4CR. The tetrazole-diketopiperazines comprise analogs of and are bioisosteric to bioactive diketopiperazines, which thus draws attention for novel bioactive compound design. This scaffold was produced to fill the screening deck of the European lead factory.

AB - A concise route for the synthesis of the novel compound class tetrazole-diketopiperazines was developed. The approach involves the use of two multicomponent reactions: the Ugi tetrazole four-component reaction (4CR) and the classical intramolecular Ugi 4CR. The tetrazole-diketopiperazines comprise analogs of and are bioisosteric to bioactive diketopiperazines, which thus draws attention for novel bioactive compound design. This scaffold was produced to fill the screening deck of the European lead factory.

KW - Multicomponent reactions

KW - Nitrogen heterocycles

KW - Ketopiperazines

KW - Screening library

KW - Isocyanides

KW - COMBINATORIAL LIBRARIES

KW - SOLID-PHASE

KW - DIKETOPIPERAZINES

KW - DERIVATIVES

KW - ISONITRILEN

KW - CHEMISTRY

KW - SURROGATE

KW - RING

KW - ZINC

U2 - 10.1002/ejoc.201403401

DO - 10.1002/ejoc.201403401

M3 - Article

SN - 1434-193X

VL - 2015

SP - 51

EP - 55

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 1

ER -

Concise Synthesis of Tetrazole-Ketopiperazines by Two Consecutive Ugi Reactions

Abstract

Keywords

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Research output

CCDC 986844: Experimental Crystal Structure Determination

CCDC 986845: Experimental Crystal Structure Determination

Datasets

CCDC 986844: Experimental Crystal Structure Determination

CCDC 986845: Experimental Crystal Structure Determination

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