Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process

© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.Multicomponent reactions are of utmost importance at generating a unique, wide, and complex chemical space. Herein we describe a novel multicomponent approach based on the combination of the isonitrile-tetrazine (4+1) cycloaddition and the Ugi four-component reaction to generate pyrazole amide derivatives. The scope of the reaction as well as mechanistic insights governing the 4H-pyrazol-4-imine tautomerization are provided. This multicomponent process provides access to a new chemical space of pyrazole amide derivatives and offers a tool for peptide modification and stapling.This work was supported by a Marie Skłodowska-Curie grant (Agreement No. 101018454) from the European Union's Horizon 2020 research and innovation program. We thank the DFG (post-doctoral fellowship, grant no. 493006134, to A. V. V.), Fundação para a Ciência e a Tecnologia (Ph.D. studentship 2022.09827.BD to A. L. D.) and MCIN/AEI/10.13039/501100011033 (PID2021-125946OB-I00 to G. J. O. and CEX2021-001136-S to CIC bioGUNE).info:eu-repo/semantics/publishedVersio

Practical aspects of real-time reaction monitoring using multi-nuclear high resolution FlowNMR spectroscopy

FlowNMR spectroscopy is an excellent technique for non-invasive real-time reaction monitoring under relevant conditions that avoids many of the limitations that bedevil other reaction monitoring techniques.</p

Mapping of N−C bond formation from a series of crystalline peri‐substituted naphthalenes by charge density and solid‐state NMR methodologies

A combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1JNC coupling measurements supported by periodic density functional theory (DFT) calculations is used to characterise the transition from an n–π* interaction to bond formation between a nucleophilic nitrogen atom and an electrophilic sp2 carbon atom in a series of crystalline peri‐substituted naphthalenes. As the N⋅⋅⋅C distance reduces there is a sharp decrease in the Laplacian derived from increasing charge density between the two groups at ca. N⋅⋅⋅C = 1.8 Å, with the periodic DFT calculations predicting, and heteronuclear spin‐echo NMR measurements confirming, the 1JNC couplings of ≈3–6 Hz for long C−N bonds (1.60–1.65 Å), and 1JNC couplings of 2.1 Å

Dreißig Jahre Fakultät Sprach- und Literaturwissenschaften an der Otto-Friedrich-Universität Bamberg (1977 bis 2007)

Anlass zur Vorlage der Festschrift ist das dreißigjährige Bestehen der Fakultät Sprach- und Literaturwissenschaften (SpLit) der Otto-Friedrich-Universität Bamberg (1977–2007). Sie soll die Entwicklung, die die Fakultät seit ihrer Gründung genommen hat, möglichst knapp und sachlich dokumentieren. Sie hat daher den Charakter einer Leistungsbilanz, sie bietet streckenweise Materialien zu einer Chronik der Fakultät, sie verschweigt aber auch nicht ihre „Geburtsfehler“ in Gestalt mangelnder Ressourcen. In einer Zeit des Umbruchs, nämlich der bevorstehenden Verschmelzung mit der Fakultät Geschichts- und Geowissenschaften (GGeo) zu einer Fakultät Geistes- und Kulturwissenschaften (GuK), soll diese Selbstdarstellung der Fakultät ihr Profil und ihre Identität bis zu ihrer zum 1.10.2007 zu Ende gegangenen selbständigen Existenz erkennbar machen. Die Druckauflage wurde vom Dekanat der Fakultät herausgegeben

Mapping of N-C bond formation from a series of crystalline peri-substituted naphthalenes by charge density and solid-state NMR methodologies

A combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1J NC coupling measurements supported by periodic density functional theory (DFT) calculations is used to characterise the transition from an n–π* interaction to bond formation between a nucleophilic nitrogen atom and an electrophilic sp 2 carbon atom in a series of crystalline peri-substituted naphthalenes. As the N⋅⋅⋅C distance reduces there is a sharp decrease in the Laplacian derived from increasing charge density between the two groups at ca. N⋅⋅⋅C = 1.8 Å, with the periodic DFT calculations predicting, and heteronuclear spin-echo NMR measurements confirming, the 1J NC couplings of ≈3–6 Hz for long C−N bonds (1.60–1.65 Å), and 1J NC couplings of &lt;1 Hz for N⋅⋅⋅C &gt;2.1 Å. </p

Merging the Isonitrile-Tetrazine (4+1) Cycloaddition and the Ugi Four-Component Reaction into a Single Multicomponent Process

&lt;p&gt;Abstract: Multicomponent reactions are of utmost importance at generating a unique, wide, and complex&lt;/p&gt;&lt;p&gt;chemical space. Herein we describe a novel multicomponent approach based on the combination of the&lt;/p&gt;&lt;p&gt;isonitrile-tetrazine (4+1) cycloaddition and the Ugi four-component reaction to generate pyrazole amide&lt;/p&gt;&lt;p&gt;derivatives. The scope of the reaction as well as mechanistic insights governing the 4H-pyrazol-4-imine&lt;/p&gt;&lt;p&gt;tautomerization are provided. This multicomponent process provides access to a new chemical space of&lt;/p&gt;&lt;p&gt;pyrazole amide derivatives and offers a tool for peptide modification and stapling.&lt;/p&gt

Merging the Isonitrile‐Tetrazine (4+1) Cycloaddition and the Ugi Four‐Component Reaction into a Single Multicomponent Process

Multicomponent reactions are of utmost importance at generating a unique, wide, and complex chemical space. Herein we describe a novel multicomponent approach based on the combination of the isonitrile‐tetrazine (4+1) cycloaddition and the Ugi four‐component reaction to generate pyrazole amide derivatives. The scope of the reaction as well as mechanistic insights governing the 4H‐pyrazol‐4‐imine tautomerization are provided. This multicomponent process provides access to a new chemical space of pyrazole amide derivatives and offers a tool for peptide modification and stapling