6.07 Ritter-Type Reactions

Bishop, Roger

doi:10.1016/b978-0-08-097742-3.00610-8

Cited by 10 publications

(6 citation statements)

References 237 publications

(188 reference statements)

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“…The intramolecular variation of the standard Ritter reaction offers a diverse variety of heterocyclic products with an imine functional group. 8 – 10 Also, there are a small number of cases involving the formation of a bridged bicyclic structure, known as the bridging Ritter product. This bridging cyclisation has been used previously by our research group to synthesise more complex alkaloid-like molecules.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative activities of alkaloid-like compounds

Rawling

Roseblade

et al. 2017

Med. Chem. Commun.

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Section: Introductionmentioning

confidence: 99%

Antiproliferative activities of alkaloid-like compounds

Rawling

Roseblade

et al. 2017

Med. Chem. Commun.

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“…Alkenes are a class of stable and easily available weak π-nucleophiles, which can only undergo transition metal-mediated C–C bond forming reactions, or react with reactive electrophiles such as acyl chlorides (Friedel-Crafts acylation of alkenes) 2 or in situ generated highly electrophilic intermediates, such as nitrilium ions [the extended Bischler–Napieralski (B–N) reaction 3 4 5 6 7 ], iminium 8 / N -acyliminium ions 9 , and acid-activated aldehydes/ketones (Prins reaction 10 ). On the other hand, although nitrilium ions are key intermediates in several classical reactions such as Houben-Hoesch 11 , Ritter 12 13 , von Braun 13 , Bischler-Napieralski 13 , Beckmann 13 , Schmidt 13 , and Ugi reactions 14 , their participation in synthetically useful intermolecular reactions with alkenes is unknown. Amides are another class of bench-stable compounds with low electrophilicity 15 16 due to the strong resonance between the π * orbital of the carbonyl group and the nitrogen lone pair.…”

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confidence: 99%

Metal-Free C–H Alkyliminylation and Acylation of Alkenes with Secondary Amides

Huang

Geng

et al. 2016

Sci Rep

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Carbon–carbon bond formation by metal-free cross-coupling of two reactants with low reactivity represents a challenge in organic synthesis. Secondary amides and alkenes are two classes of bench-stable compounds. The low electrophilicity of the former and low nucleophilicity of the latter make the direct coupling of these two partners challenging yet highly desirable. We report herein an unprecedented intermolecular reaction of secondary amides with alkenes to afford α,β-unsaturated ketimines or enones, which are versatile intermediates for organic synthesis and are prevalent in bioactive compounds and functional materials. Our strategy relies on the chemoselective activation of the secondary amide with trifluoromethanesulfonic anhydride (Tf2O)/2-fluoropyridine to generate a highly reactive nitrilium intermediate, which reacts efficiently with alkenes. This metal-free synthesis is characterized by its mild reaction conditions, excellent functional group tolerance and chemoselectivity, allowing the preparation of multi-functionalized compounds without using protecting groups.

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“…For example, sodium chloride and sodium bromide were used as redox catalysts in a CH 3 CN-saturated NaCl aqueous (pH 4) solvent mixture using platinum as the working electrode for the electrochemical oxidation of cyclic aziridines to form keto nitriles in an 80% yield [ 63 ]. Keto nitriles are valuable intermediates for various synthetic transformations [ 64 ]. This reaction was explained by the generation of an azaallenyl intermediate cation, which is hydrated to form an α-hydroxyimine.…”

Section: Aliphatic Aminesmentioning

confidence: 99%

Mechanistic Aspects of the Electrochemical Oxidation of Aliphatic Amines and Aniline Derivatives

Mruthunjaya

Torriero

2023

Molecules

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The electrochemical oxidation of amines is an essential alternative to the conventional chemical transformation that provides critical routes for synthesising and modifying a wide range of chemically useful molecules, including pharmaceuticals and agrochemicals. As a result, the anodic reactivity of these compounds has been extensively researched over the past seven decades. However, the different mechanistic aspects of the electrochemical oxidation of amines have never been discussed from a comprehensive and general point of view. This review examines the oxidation mechanism of aliphatic amines, amides, aniline and aniline derivatives, carbamates, and lactams, either directly oxidised at different electrode surfaces or indirectly oxidised by a reversible redox molecule, in which the reactive form was generated in situ. The mechanisms are compared and simplified to understand all possible pathways for the oxidation of amines using only a few general mechanisms. Examples of the application of these oxidation reactions are also provided.

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6.07 Ritter-Type Reactions

Cited by 10 publications

References 237 publications

Antiproliferative activities of alkaloid-like compounds

Antiproliferative activities of alkaloid-like compounds

Metal-Free C–H Alkyliminylation and Acylation of Alkenes with Secondary Amides

Mechanistic Aspects of the Electrochemical Oxidation of Aliphatic Amines and Aniline Derivatives

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