New approach to oligotriazoles using a cobalt complex of propargyl azides as a synthetic component

Tsukada, Yuichi; Yamada, Kohei; Kunishima, Munetaka

doi:10.1016/j.tetlet.2011.04.082

Cited by 12 publications

(4 citation statements)

References 23 publications

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“…Reactions of the dimer 3.22 with methyl azidoacetate afforded a triazolamer 3.23 (Scheme 3.4). 85 4-Bromo-1-butyne was used as the starting material for the synthesis of "-CH2-CH2-" linked triazolamers. Thus, CuAAC coupling of 4-Bromo-1-butyne with benzyl or n-octyl azide afforded the monomeric bromotriazoles 3.24a in excellent yields.…”

Section: Scheme 33mentioning

confidence: 99%

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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A typical 1,2,3-triazoles are important aromatic heterocyclic compounds with three adjacent nitrogen atoms. These "unnatural" heterocycles found applications in pharmaceutical science, material science and chemical biology. Oligo-1,2,3-triazole linked molecules showed interesting applications in the field of DNA binding, selfassembly, surface modification, supramolecular chemistry etc. In this article, oligo-1,2,3-triazoles are broadly classified into two categories: (i) 1,2,3-triazoles are connected through varieties of organic molecules and (ii) triazole units are connected with one another either by N-(CH)n-C linkages or by amide bonds generated from amino acids. Syntheses and properties of some of these oligomers are reviewed in this article.

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Section: Scheme 33mentioning

confidence: 99%

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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“…[490] Oligo-triazoles could be synthesized by use of dicobalthexacarbonyl complexes of propargylazides. [491] D. Astruc and co-workers reported on the syntheses (and properties) of a series of triazole containing dendrimers, polymers and nanoparticles by click chemistry. [492] To conclude this short chapter, we refer to the blockbuster already exposed in the Introduction: the perfect inorganic version of the click reaction between Ph 3 PAuN 3 and PhCϵCAuPPh 3 as performed in the group of Veige (Equation (22)).…”

Section: Reactions Of Main Group Element Azides With Alkynesmentioning

confidence: 99%

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Fehlhammer

Beck

2015

Zeitschrift anorg allge chemie

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Abstract. In whatever state of bonding -whether covalent to an organic residue or a heteroatom, or polar to ionic in contact with a metal -the azide moiety N 3 is characterized by its high potential of reactivity which essentially manifests itself in two basic processes: the elimination of dinitrogen and the entry into 1,3-dipolar cycloadditions with suitable dipolarophiles, the latter of which clearly predominates the chemistry of azide, also that of its metal compounds. In a preceding review entitled "Part I -Metal Azides: Overview, General Trends and Recent Developments" which was meant to lay the foundations for the present paper, these and other reactions have already been touched upon. The present review -Part II -now focusses in great detail on the formation of five-membered heterocyclestetrazol(at)es, triazol(at)es, triazolin(at)es, thiatriazol(at)es, etc. as well as various consecutive products -from azide and nitriles, isocyanides, alkynes, alkenes and heteroallenes (CS 2 , RN=C=S) in the ligand sphere of the metal. Generally, these [3+2]-cycloadditions are found to CONTENTS

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“…178 The substitution of a leaving group, such as propargylic acetate, with heteroatom-and carbon-based nucleophiles is highly chemoselective in that it avoids the formation of allenes. Recent investigations of heteroatom nucleophiles involve the formation of bispropargylic ethers, 179 cyclic polyethers, 180,181 propargylic azides, 182 dithia-and thia-oxacyclooctynes, 183 seven-and eight-membered cyclic ethers 184 and carbacycles [185][186][187] with a cobalt-protected triple bond as well as the formation of 5-alkynylproline derivatives. 188 The dicobalt hexacarbonyl moiety is able to stabilise cationic species which can be attacked by nucleophiles.…”

Section: Nicholas Reactionsmentioning

confidence: 99%

Cobalt-Catalysed Bond Formation Reactions; Part 2

Röse

Hilt

2015

Synthesis

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This review summarises the cobalt-catalysed reactions of the years 2008 through 2014. Covered are addition reactions, such as the hydrogenation of double bonds, the addition of C-H bonds to double and triple bonds, C-H activation reactions, cobalt-catalysed cross-coupling reactions and selected additions of H-B and H-Si bonds to unsaturated starting materials. The cobalt-catalysed cycloadditions range from cyclopropanations, [2+2], Pauson-Khand reactions, [2+2+2], [4+2], [6+2] cycloadditions as well as benzannulations. Also covered are Nicholas reactions, cobalt-catalysed Jacobsen's kinetic resolution of epoxides as well as selected miscellaneous cobalt-catalysed processes mainly for carbon-carbon bond formations. 1 Introduction 2 Addition Reactions 3 Homo-and Cross-Coupling Reactions 4 Jacobsen Kinetic Resolution of Epoxides 5 Nicholas Reactions 6 Cycloaddition Reactions 7 Miscellaneous 8 Conclusion

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New approach to oligotriazoles using a cobalt complex of propargyl azides as a synthetic component

Cited by 12 publications

References 23 publications

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Cobalt-Catalysed Bond Formation Reactions; Part 2

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New approach to oligotriazoles using a cobalt complex of propargyl azides as a synthetic component

Cited by 12 publications

References 23 publications

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Azide Chemistry – An Inorganic Perspective, Part II[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Cobalt-Catalysed Bond Formation Reactions; Part 2

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Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems