ChemInform Abstract: SYNTHESIS OF AROMATIC HYDROCARBONS FROM 1,2,3‐SELENADIAZOLES AND α‐PYRONES

Meier, Herbert; Molz, Thomas; Merkle, U.; Echter, Toni; Lorch, Margret

doi:10.1002/chin.198233135

Cited by 3 publications

(3 citation statements)

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“…Controllable, site-specific reactions are highly valuable for multiplexing of (bio)molecules and expansion of labeling diversity. Early studies during the 1970s and 1980s described the reaction of plain cyclooctyne with various 1,2-quinones in organic solvents. − It has also been shown that 1,2-quinones can be generated on proteins by selective periodate oxidation of genetically incorporated 3,4-dihydroxy- l -phenylalanine ( l -DOPA), leading to slow (5 h) conjugation with a polysaccharide . We aimed to explore the facile catechol-to-quinone conversion as a fast, chemically activatable bioconjugation by strain-promoted chemistry.…”

Section: Introductionmentioning

confidence: 99%

Strain-Promoted Oxidation-Controlled Cyclooctyne–1,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation

et al. 2015

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A main challenge in the area of bioconjugation is to devise reactions that are both activatable and fast. Here, we introduce a temporally controlled reaction between cyclooctynes and 1,2-quinones, induced by facile oxidation of 1,2-catechols. This so-called strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) shows a remarkably high reaction rate when performed with bicyclononyne (BCN), outcompeting the well-known cycloaddition of azides and BCN by 3 orders of magnitude, thereby allowing a new level of orthogonality in protein conjugation.

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Section: Introductionmentioning

confidence: 99%

Strain-Promoted Oxidation-Controlled Cyclooctyne–1,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation

et al. 2015

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“…Another [4 + 2] IEEDA cycloaddition reaction is the reaction between an ortho -quinone (e.g. 31 ) and a cyclooctyne ( 32 ) under formation of diketone 33 (Figure A) or between ortho -quinone 34 and olefin 35a /alkyne 35b to form bicyclo[2.2.2]octadiene diketone 36a or 36b (Figure B). , Applications of this reaction in more complex settings will be treated below; here we focus on the model studies that were used in order to determine the rates, scope, and limitations of this conversion. Specifically, the model substrate 4- tert -butyl-1,2-benzoquinone 34 was used to determine the reaction rate constants with various strained alkenes and alkynes (Figure C).…”

Section: Small Moleculesmentioning

confidence: 99%

Oxidation-Induced “One-Pot” Click Chemistry

et al. 2021

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Click chemistry has been established rapidly as one of the most valuable methods for the chemical transformation of complex molecules. Due to the rapid rates, clean conversions to the products, and compatibility of the reagents and reaction conditions even in complex settings, it has found applications in many molecule-oriented disciplines. From the vast landscape of click reactions, approaches have emerged in the past decade centered around oxidative processes to generate in situ highly reactive synthons from dormant functionalities. These approaches have led to some of the fastest click reactions know to date. Here, we review the various methods that can be used for such oxidation-induced “one-pot” click chemistry for the transformation of small molecules, materials, and biomolecules. A comprehensive overview is provided of oxidation conditions that induce a click reaction, and oxidation conditions are orthogonal to other click reactions so that sequential “click-oxidation-click” derivatization of molecules can be performed in one pot. Our review of the relevant literature shows that this strategy is emerging as a powerful approach for the preparation of high-performance materials and the generation of complex biomolecules. As such, we expect that oxidation-induced “one-pot” click chemistry will widen in scope substantially in the forthcoming years.

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“…5 Tribenzo[ a , c , f ]cyclooctanes are primarily synthesized by Diels–Alder reaction of strained acetylenes with cyclic dienes including α-pyrones (Fig. 1, a) 6 and furan (Fig. 1, b) 7 followed by subsequent deoxygenation.…”

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confidence: 99%

Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C–H arylation for the construction of tribenzo[a,c,f]cyclooctanones

2022

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ChemInform Abstract: SYNTHESIS OF AROMATIC HYDROCARBONS FROM 1,2,3‐SELENADIAZOLES AND α‐PYRONES

Abstract: Die Selenadiazole (I), (IV), (VI), (VIII), (X) und (XII) spalten beim Erhitzen Se und N2 ab unter Bildung der entsprechenden Cycloalkine, die in situ mit α‐Pyron (II) zu den literaturbekannten Aromaten (III), (V), (VII), (IX).

Cited by 3 publications

References 1 publication

Strain-Promoted Oxidation-Controlled Cyclooctyne–1,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation

Strain-Promoted Oxidation-Controlled Cyclooctyne–1,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation

Oxidation-Induced “One-Pot” Click Chemistry

Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C–H arylation for the construction of tribenzo[a,c,f]cyclooctanones

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