Synthesis and reactivity of 4-lithium and 4-copper derivatives of sydnone imines

Cherepanov, I. A.; Калинин, В. Н.

doi:10.1070/mc2000v010n05abeh001319

Cited by 20 publications

(11 citation statements)

References 7 publications

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“…13 C NMR (100 MHz, CDCl 3 ): δ = 174.4 (o, C‐5), 174.2 (o, C‐7), 137.1 (o, C‐8), 129.3 (+, C‐11), 129.3 (+, C‐9/9′), 127.9 (+, C‐10/10′), 104.0 (+, C‐4), 64.6 (+, C‐12), 32.2 (–, C‐13/13′), 24.6 (–, C‐14/14′), 24.5 (–, C‐15) ppm. Spectroscopic data are in agreement with those reported in the literature …”

Section: Methodssupporting

confidence: 91%

“…The sydnone imine hydrochlorides 6a , b were prepared from the amines 5a , b by nucleophilic substitution with haloacetonitriles in reasonable yields according to modified literature procedures concerning the cyclohexyl derivative, followed by N ‐nitrosation and ring closure reaction upon treatment with gaseous hydrochloric acid. Finally, benzoylation gave the sydnone imines 7a , b as stable, brownish to yellow compounds, which we used as starting materials for further syntheses.…”

Section: Resultsmentioning

confidence: 99%

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Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

et al. 2018

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Sydnone imines were deprotonated at the C4 position to give lithium‐stabilized anions, which proved to be stable for several months in solution. These anions are elements of the intersection of the substance classes of N‐heterocyclic carbenes and mesomeric betaines. They can be formulated as anionic N‐heterocyclic carbenes. The negative charge translates into high‐field shifts of the 13C NMR resonance frequencies of C4 in comparison to other NHCs. Similar to the chemistry of N‐heterocyclic carbenes, reactions with isocyanates and isothiocyanates gave 4‐(N‐carbamoyl)‐benzoylsydnone imines in trapping reactions. As a result of ring transformations involving the characteristic π‐architecture of the mesoionic framework, imidazolidine‐2,4‐dithiones, imidazolin‐2,4‐diones and 1,2,4‐triazol‐5‐ones were formed depending on the substitution pattern of the starting materials and the reaction conditions.

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Section: Methodssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

et al. 2018

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“…68,69 The base nBuLi initiated several electrophilic attacks despite of a restricted nucleophilicity of C4 in accordance with some literature data, 70 however, rapid decomposition at elevated temperatures occurred. 71,72 We finally found that quantitative deprotonation of Molsidomine 7a and sydnone imine 7b to give the carbenes 8a,b can be achieved on addition of 1M lithium bis(trimethylsilyl)amide in THF at rt (Scheme 4).…”

Section: Scheme 2 Resonance Forms Of Molsidomine 7a and Of Its Anionmentioning

confidence: 99%

Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold

et al. 2017

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“…Anionic iminosydnone NHC may be trapped in a form of gold or palladium complexes by a treatment with Ph 3 PAuCl and (Ph 3 P) 2 PdCl 2 , respectively. N 3 -aryl and N 3 -morpholinylsydnone imine carbene Pd complexes were tested as catalysts in Suzuki–Miyaura and Sonogashira–Hagihara cross-coupling reactions [ 45 ].…”

Section: Sydnone Iminesmentioning

confidence: 99%

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Ферштат

Zhilin

2021

Molecules

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Nitric oxide (NO) is a key signaling molecule that acts in various physiological processes such as cellular metabolism, vasodilation and transmission of nerve impulses. A wide number of vascular diseases as well as various immune and neurodegenerative disorders were found to be directly associated with a disruption of NO production in living organisms. These issues justify a constant search of novel NO-donors with improved pharmacokinetic profiles and prolonged action. In a series of known structural classes capable of NO release, heterocyclic NO-donors are of special importance due to their increased hydrolytic stability and low toxicity. It is no wonder that synthetic and biochemical investigations of heterocyclic NO-donors have emerged significantly in recent years. In this review, we summarized recent advances in the synthesis, reactivity and biomedical applications of promising heterocyclic NO-donors (furoxans, sydnone imines, pyridazine dioxides, azasydnones). The synthetic potential of each heterocyclic system along with biochemical mechanisms of action are emphasized.

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Synthesis and reactivity of 4-lithium and 4-copper derivatives of sydnone imines

Cited by 20 publications

References 7 publications

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

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