Novel Process for the Synthesis of Class I Antiarrhythmic Agent (±)-Cibenzoline and Its Analogs

Gholap, Atul R.; Paul, Vincent; Srinivasan, Kumar

doi:10.1080/00397910802006388

Cited by 8 publications

(7 citation statements)

References 23 publications

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“…3,3-Diphenylacrylonitrile was isolated and the obtained 1 H NMR was in agreement with the literature (14,15). The formation of benzophenone was verified with a standard.…”

Section: Methodssupporting

confidence: 84%

“…Three other, much smaller fractions, contained compounds that were possible to identify: 3,3‐diphenylacrylonitrile, benzophenone and 2‐ethylhexyl 2‐ethoxy‐4‐phenylquinoline‐3‐carboxylate. 3,3‐Diphenylacrylonitrile was isolated and the obtained 1 H NMR was in agreement with the literature (14,15). The formation of benzophenone was verified with a standard.…”

supporting

confidence: 86%

“…The main compound formed in the photolysis experiment was ethyl 2‐cyano‐3,3‐diphenyl acrylate. It was isolated as a white solid and the obtained NMR spectra were in accordance with reference (14). Three other, much smaller fractions, contained compounds that were possible to identify: 3,3‐diphenylacrylonitrile, benzophenone and 2‐ethylhexyl 2‐ethoxy‐4‐phenylquinoline‐3‐carboxylate.…”

mentioning

confidence: 59%

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Investigation of the Sunscreen Octocrylene’s Interaction with Amino Acid Analogs in the Presence of UV Radiation

Karlsson

Persson

Mårtensson

et al. 2012

Photochem & Photobiology

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Octocrylene is an organic UV filter, commonly used in sunscreens and cosmetics, which can give rise to both contact and photocontact allergy. Our aim was to investigate octocrylene's interaction with amino acid analogs in the presence of UV radiation to better understand the reason for octocrylene's photoallergenic capacity. The amino acid analogs were photolysed in presence and absence of octocrylene for 1 h in cyclohexane. The rate of degradation was considerably slower for all amino acid analogs when octocrylene was present in the mixture. Benzylamine, the lysine analog, did react with octocrylene during the photolysis and the corresponding amide was formed in an acylation reaction. By varying the benzylamine concentration and keeping the octocrylene concentration fixed the reaction rate was shown to be independent of the amine concentration. The same type of acylation reaction took place when octocrylene alone was photolysed in ethanol in which the ethyl ester was formed from octocrylene and ethanol. Our results suggest that octocrylene's ability to cause photocontact allergy could be due to its photoinduced reactivity toward primary amines and alcohols.

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“…3,3-Diphenylacrylonitrile was isolated and the obtained 1 H NMR was in agreement with the literature (14,15). The formation of benzophenone was verified with a standard.…”

Section: Methodssupporting

confidence: 84%

supporting

confidence: 86%

mentioning

confidence: 59%

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Investigation of the Sunscreen Octocrylene’s Interaction with Amino Acid Analogs in the Presence of UV Radiation

Karlsson

Persson

Mårtensson

et al. 2012

Photochem & Photobiology

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“…When the reaction was performed at 70 °C, the yield of the condensation product 3a was improved to 56% using the same catalyst loading under solvent-free conditions (Table , entry 2). The Knoevenagel product, 3a , was confirmed by 1 H NMR spectroscopic data and comparison with literature data. − A decrease in reaction yield was noted when we performed the reaction using a lower catalyst loading (Table , entry 3). Next, we studied the effect of solvent on the catalytic reaction in the presence of 10 mol % nanocatalyst (Y 2 ZnO 4 ).…”

Section: Resultssupporting

confidence: 53%

“…Under the optimized condition, aromatic carbonyl compounds reacted smoothly with malononitrile and afforded the corresponding Knoevenagel condensation products ( 3j–l ) within a short period of time, as shown in Table (entries 10–12). The structure of all products ( 3a–l ) was determined by 1 H NMR data and comparison with literature data. − Compared to the reported methods, our method under microwave conditions is environmentally friendly and has several advantages including a short reaction time and solvent-free conditions with excellent conversion and yields. Moreover, the reaction does not require any additive or activators and the nanocatalyst used in the reaction is easily recoverable and recyclable.…”

Section: Resultsmentioning

confidence: 99%

New Dual-Functional and Reusable Bimetallic Y₂ZnO₄ Nanocatalyst for Organic Transformation under Microwave/Green Conditions

et al. 2020

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A novel bimetallic and reusable Y 2 ZnO 4 nanocatalyst was synthesized by a simple coprecipitation method. The prepared nanocatalyst exhibited dual catalytic activity and was characterized using X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), and scanning electron microscopy (SEM). The average crystallite and grain sizes were found to be 17 ± 1 and 10 ± 2 nm, respectively. On the one hand, the catalytic activity of the nanocatalyst was studied for the Knoevenagel condensation reaction of aromatic aldehydes with active methylene compounds, such as ethyl cyanoacetate and malononitrile, under microwave irradiation and solvent-free conditions. On the other hand, the nanoparticles also showed faster photocatalytic activity against methyl orange (MO) compared to other dyes. The nanocatalyst was easily recoverable by a simple filtration method and was recycled without any significant loss of catalytic activity. The advantages of this nanocatalyst were a simple workup procedure, high reaction yields, solvent-free conditions, reusability, and a short reaction time under green reaction conditions.

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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Novel Process for the Synthesis of Class I Antiarrhythmic Agent (±)-Cibenzoline and Its Analogs

Cited by 8 publications

References 23 publications

Investigation of the Sunscreen Octocrylene’s Interaction with Amino Acid Analogs in the Presence of UV Radiation

Investigation of the Sunscreen Octocrylene’s Interaction with Amino Acid Analogs in the Presence of UV Radiation

New Dual-Functional and Reusable Bimetallic Y₂ZnO₄ Nanocatalyst for Organic Transformation under Microwave/Green Conditions

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

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Novel Process for the Synthesis of Class I Antiarrhythmic Agent (±)-Cibenzoline and Its Analogs

Cited by 8 publications

References 23 publications

Investigation of the Sunscreen Octocrylene’s Interaction with Amino Acid Analogs in the Presence of UV Radiation

Investigation of the Sunscreen Octocrylene’s Interaction with Amino Acid Analogs in the Presence of UV Radiation

New Dual-Functional and Reusable Bimetallic Y2ZnO4 Nanocatalyst for Organic Transformation under Microwave/Green Conditions

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

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Product

Resources

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New Dual-Functional and Reusable Bimetallic Y₂ZnO₄ Nanocatalyst for Organic Transformation under Microwave/Green Conditions