Condensation of Aromatic Nitro Compounds with Arylacetonitriles. V. Some Reactions of the Arylcyanomethylenequinone Oximes.

Davis, Ralph B.; Weber, John D.

doi:10.1021/je60019a033

Cited by 5 publications

(8 citation statements)

References 3 publications

(4 reference statements)

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“…This reaction, due to its stoichiometry, can be considered as an intramolecular redox process with release of hydroxide anion. This conversion proceeds usually in protic solvents apparently via protonation of the negatively charged NO 2 group of the σ H -adducts and elimination of water and is often followed by further transformations of the produced nitroso compounds. ,− The reaction shown in Scheme 1 (path 1b) proceeds along this pathway. Similar conversion can be promoted by treatment of σ H -adducts with protic acids, Lewis acids, , or silylating agents. − …”

Section: 2 Conversion Of σH-adducts Into Nitroso Compoundsmentioning

confidence: 99%

Nucleophilic Substitution of Hydrogen in Heterocyclic Chemistry

2004

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Section: 2 Conversion Of σH-adducts Into Nitroso Compoundsmentioning

confidence: 99%

Nucleophilic Substitution of Hydrogen in Heterocyclic Chemistry

2004

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“…Analogues of arylcyanomethylenequinone oximes 12aa-cn. In 1964, Davis [70] patented another example of condensation of benzyl cyanide 1a with 4-chloronitrobenzene 2b. The author described that in a course of reaction, the expected arylcyanomethylenequinone oxime is not created but an analogue of isoxazole 13 is formed as the only product (Scheme 7).…”

Section: The Condensation Of (Hetero) Arylacetonitriles With Nitro (H...mentioning

confidence: 99%

“…An example of this reduction process is the reaction of 4-(phenylcyanomethylene)-cyclohexa-2,5-dien-1-one oxime 3a and its analogues 12ad-12ak and 38ba-da. In the effect, the 4-(arylcyanomethyl)-arylamines 39a and 39ad-39da were synthesized [54][55][56]80,97]. The reactions were realized using zinc and acetic acid in methanolic solution (Scheme 16).…”

Section: The Reduction Reactions Of Arylcyanomethylenequinone Oximementioning

confidence: 99%

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Arylcyanomethylenequinone Oximes: An Overview of Synthesis, Chemical Transformations, and Biological Activity

Kula,

Nagatsky,

Sadowski

et al. 2023

Molecules

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Quinone methides are a class of biologically active compounds that can be used in medicine as antibacterial, antifungal, antiviral, antioxidant, and anti-inflammatory agents. In addition, quinone methides have the potential to be used as pesticides, dyes, and additives for rubber and plastics. In this paper, we discuss a subclass of quinone methides: methylenequinone oximes. Although the first representatives of the subgroup were synthesized in the distant past, they still need to be additionally studied, while their chemistry, biological properties, and perspective of practical applications require to be comprehensively summarised. Based on the analysis of the literature, it can be concluded that methylenequinone oximes exhibit a diversified profile of properties and outstanding potential as new drug candidates and reagents in organic synthesis, both of electrophilic and nucleophilic nature, worthy of wide-ranging further research.

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“…This reaction can be considered as an intramolecular redox process with release of hydroxide ion. This conversion occurs usually in protic solvents apparently via protonation of the negatively charged oxygen of nitro group of the δ H ‐adducts and elimination of water [4–7]. These nitrosoarenes are mostly cyclized to heterocyclic systems under the reaction conditions [8–12].…”

Section: Introductionmentioning

confidence: 99%