Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids

Constantinos G. Neochoritis; Tryfon Zarganes-Tzitzikas; Michaela Novotna; Tatiana Mitrikova; Zefeng Wang; Katarzyna Kurpiewska; Justyna Kalinowska-Tluscik; Alexander Domling

doi:10.1002/ejoc.201901187

Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids

Constantinos G. Neochoritis, Tryfon Zarganes-Tzitzikas, Michaela Novotna, Tatiana Mitrikova, Zefeng Wang, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Alexander Domling^*

^*Corresponding author for this work

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

7 Citations (Scopus)

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Abstract

Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.

Original language	English
Pages (from-to)	6132-6137
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	35
DOIs	https://doi.org/10.1002/ejoc.201901187
Publication status	Published - 22-Sept-2019

Keywords

Multicomponent reactions
Boron
Ugi reaction
C-C coupling
Structure elucidation
BORONIC ACIDS
PYRAZINES
PLATFORM
ANALOGS

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10.1002/ejoc.201901187

Isocyanide-Based Multicomponent Reactions of Free Phenylboronic AcidsFinal publisher's version, 1.45 MBLicence: Taverne

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CCDC 1819623: Experimental Crystal Structure Determination
Neochoritis, C. G. (Contributor), Zarganis Tzitzikas, T. (Contributor), Novotná, M. (Contributor), Mitríková, T. (Contributor), Wang, Z. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 26-Jan-2018
DOI: 10.5517/ccdc.csd.cc1z2gj1
Dataset

Cite this

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title = "Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids",

abstract = "Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.",

keywords = "Multicomponent reactions, Boron, Ugi reaction, C-C coupling, Structure elucidation, BORONIC ACIDS, PYRAZINES, PLATFORM, ANALOGS",

author = "Neochoritis, {Constantinos G.} and Tryfon Zarganes-Tzitzikas and Michaela Novotna and Tatiana Mitrikova and Zefeng Wang and Katarzyna Kurpiewska and Justyna Kalinowska-Tluscik and Alexander Domling",

year = "2019",

month = sep,

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doi = "10.1002/ejoc.201901187",

language = "English",

volume = "2019",

pages = "6132--6137",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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TY - JOUR

T1 - Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids

AU - Neochoritis, Constantinos G.

AU - Zarganes-Tzitzikas, Tryfon

AU - Novotna, Michaela

AU - Mitrikova, Tatiana

AU - Wang, Zefeng

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tluscik, Justyna

AU - Domling, Alexander

PY - 2019/9/22

Y1 - 2019/9/22

N2 - Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.

AB - Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.

KW - Multicomponent reactions

KW - Boron

KW - Ugi reaction

KW - C-C coupling

KW - Structure elucidation

KW - BORONIC ACIDS

KW - PYRAZINES

KW - PLATFORM

KW - ANALOGS

U2 - 10.1002/ejoc.201901187

DO - 10.1002/ejoc.201901187

M3 - Article

SN - 1434-193X

VL - 2019

SP - 6132

EP - 6137

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids

Abstract

Keywords

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Handle.net

Datasets

CCDC 1819623: Experimental Crystal Structure Determination

Cite this