Creation of thio and selenocyanate derivatives of 4-quinolone <i>via</i> regioselective C–H bond functionalization under ambient conditions

Ghosh, Prasanjit; Chhetri, Gautam; Nandi, Aritra Kumar; Sarkar, Sagar; Saha, Tilak; Das, Sajal

doi:10.1039/c9nj01922g

Cited by 19 publications

(14 citation statements)

References 48 publications

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“…[20] During the same year, Ghosh and colleagues developed and implemented a mild and unique strategy for the insertion of a SeCN-precursor at C-3 position of 2-substituted 4-quinolone 38 derivatives employing KSeCN with potassium peroxydisulfate (K 2 S 2 O 8 ) as an oxidant for the transition-metal-free straightforward selenocyanation reaction in DMSO at room temperature in high to excellent yields 39. [21] A wide variety of substituted 4quinolone derivatives with electron-releasing groups (À Methyl, À Ethyl, and tert-butyl) and electron-withdrawing groups (4-Fluoro, 4-Bromo, and 4-Chloro) at the C-2 position enclosing an aryl generated high yields of the desired 3-selenocyanato products (39 a-39 f). Note that the electronic effects of 4quinolones with various substituents on the aromatic sphere at C-6 and C-8 locations were investigated and the selenocyanated products (39 g and 39 h) were easily acquired in high yield.…”

Section: Electrophilic Selenocyanation Reactionmentioning

confidence: 99%

Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry

Karmaker

Huo

2022

Asian J Org Chem

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The incorporation of the cyanato‐chalcogen group (OCN, SCN, and SeCN) has piqued the interest of many researchers in the field of modern organic synthetic chemistry. Methodologies for selenocyanation are far less advanced than those for OCN and SCN chemistry due to the scarcity of SeCN transfer reagents and synthetic approaches. It has also been discovered that the selenocyanate precursor (SeCN) performs significantly better than the thiocyanate (SCN) precursor in terms of pharmacological properties of organic scaffolds. Recent years, new reagents (nucleophilic, electrophilic, radical) and techniques were introduced that allowed the creation of the selenocyanato group uncomplicatedly under gentle reaction conditions, particularly in transition metal catalysis and photo‐/electro‐chemically influenced reactions, which were seemingly unimaginable. In this review, we have categorized a variety of techniques using various types of selenocyanate regents and their applications in the last decades, focusing on multiple catalysts for the preparation of organic selenocyanates and their derivatives.

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Section: Electrophilic Selenocyanation Reactionmentioning

confidence: 99%

Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry

Karmaker

Huo

2022

Asian J Org Chem

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“…( 3-(Bis(methylthio)methyl)-4-methylquinolin-2(1H)-one (18). Following general procedure B, with compound 27 (35 mg, 0.12 mmol) as starting material, compound 18 was obtained as a pale yellow solid (24 mg, 74%): 1 3-(Bis(ethylthio)methyl)-4-methylquinolin-2(1H)-one (19). Following general procedure B, with compound 29 (18 mg, 0.06 mmol) as starting material, compound 19 was obtained as a pale yellow solid (12 mg, 73%): 1 H NMR (400 MHz, CDCl 3 ) δ 1.34 (t, J = 7.4 Hz, 6H), 2.74 (q, J = 7.4 Hz, 4H), 2.81 (s, 3H), 6.16 (s, 1H), 7.24 (t, J = 7.4, 1H), 7.37 (d, J = 8.2 Hz, 1H), 7.49 (d, J = 7.8 Hz, 1H), 7.76 (d, J = 8.5 1H), 12.28 (s, 1H); 13 (E)-2-(2-Methoxyvinyl)quinolin-4(1H)-one (4) and 3-(Dimethoxymethyl)-4-methylquinolin-2(1H)-one (16).…”

Section: N-(2-acetylphenyl)-3-(dimethylamino)propanamide (35)mentioning

confidence: 99%

“…Best known of these are the synthetic fluoroquinolones, which possesses significantly different substitution patterns from the naturally occurring 2-alkyl-4-quinolones, but the latter class and its derivatives have also been reported to have antimicrobial properties. 3-Thiocyanate- and selenocyanate-substituted 4-arylquinolones have been shown to possess moderate antimicrobial properties against both Gram-positive and Gram-negative bacteria . In a report by Salvaggio and co-workers, a small suite of quinolone natural products was synthesized using a Suzuki–Miyaura coupling, several members of which were found to retard the growth of E. coli and S. aureus in vitro .…”

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confidence: 99%

“…3-Thiocyanate-and selenocyanatesubstituted 4-arylquinolones have been shown to possess moderate antimicrobial properties against both Gram-positive and Gram-negative bacteria. 19 In a report by Salvaggio and coworkers, a small suite of quinolone natural products was synthesized using a Suzuki−Miyaura coupling, several members of which were found to retard the growth of E. coli and S. aureus in vitro. 20 The same method has been used to produce Burkholderia-derived quinolones, which possess antimicrobial properties against Gram-positive bacteria.…”

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Synthesis of Natural and Unnatural Quinolones Inhibiting the Growth and Motility of Bacteria

Clark

2020

J. Nat. Prod.

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Synthesis of a recently discovered S-methylated quinolone natural product (1) was carried out, in addition to the production of a range of 2-substituted 4-quinolone derivatives (2–11). Two approaches were used: (i) the base-catalyzed cyclization of N-(ketoaryl)amides; (ii) attachment of the substituent to the quinolone core via a Suzuki–Miyaura cross-coupling. Also produced were a small suite of related 2(1H)-quinolones (12–19). The synthesized compounds were assessed for their antimicrobial properties. The alkene-substituted 4-quinolone 8 significantly inhibited the growth of a Pseudomonas aeruginosa strain, and both 4-quinolones and 2(1H)-quinolones were capable of inhibiting the swarming behavior of Bacillus subtilis.

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“…The proposed mechanism for the synthesis of thio /selenocyanate derivatives is shown below in figure 16. [60]…”

Section: Synthesis Of 4-quinolones Using An Organic/inorganic Catalystmentioning

confidence: 99%

Recent Developments in the Synthetic Strategies of 4‐Quinolones and Its Derivatives

2020

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The ubiquitous presence of 4-quinolones and its derivatives in a wide range of natural as well as synthetic drug molecules made them molecule of utmost importance for organic and medicinal chemists. Their wide array of biological activities such as antimicrobial, anticancer, anti-HIV, genitourinary infection, antifilarial, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Moreover, they are valuable intermediates for the synthesis of various fused heterocyclic compounds of synthetic and medicinal importance. Considering their array of synthetic and biological importance, new strategies for the synthesis of 4-quinolones and their derivatives have been designed and successfully demonstrated by researchers around the globe. The present review covers recent advances in the synthetic chemistry of 4quinolones since 2015 along with an insight into their mechanistic studies. We hope that the review article will serve as a valuable tool for the scientific community engaged in the synthesis and utilization of 4-quinolones and their derivatives.

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Creation of thio and selenocyanate derivatives of 4-quinolone via regioselective C–H bond functionalization under ambient conditions

Abstract: An operationally simple C–SCN and C–SeCN bond formation technique to generate different SCN/SeCN substituted 4-quinolone derivatives using NH4SCN/KSeCN in excellent yields was developed.

Cited by 19 publications

References 48 publications

Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry

Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry

Synthesis of Natural and Unnatural Quinolones Inhibiting the Growth and Motility of Bacteria

Recent Developments in the Synthetic Strategies of 4‐Quinolones and Its Derivatives

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