An efficient synthesis of ferrocenyl-containing 1,3,4-oxadiazole derivatives via oxidative cyclization reaction

Cin, Günseli Turgut; Verep, G.; Topel, Seda Demirel; Ciger, V.

doi:10.1007/s10593-013-1344-8

Cited by 10 publications

(7 citation statements)

References 19 publications

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“…Based on our experimental data and previous report, 8,15,22 a plausible reaction mechanism for the formation of 1,5-fused 1,2,4-triazole 6 (≡ 2a) is proposed (Scheme 2). According to this route, chloramine-T transfers the Cl + ion to the N-arylamidine 1a and generates N-chloroamidinium cation 2′ and p-toluenesulfonamide anion 3 as a proton acceptor.…”

Section: Syn Thesissupporting

confidence: 54%

A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

et al. 2019

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A convenient synthesis of 1,5-fused 1,2,4-triazoles from readily available N-arylamidines is reported. The reaction is efficiently promoted by chloramine-T to afford the desired products mostly in high yields and in relatively short time, through direct metal-free oxidative N−N bond formation. The mild nature of the synthesis and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

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Section: Syn Thesissupporting

confidence: 54%

A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

et al. 2019

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“…Following hydrazinide 6A conjugation, iminolate 6B was formed, which was then converted into target 4 via intramolecular nucleophilic substitution to give intermediate 7 , followed by the removal of a hydrogen chloride molecule (see Scheme 4). [ 72,73 ]…”

Section: Resultsmentioning

confidence: 99%

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Sanad

Mekky

Ahmed

2022

Archiv der Pharmazie

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A new series of pyrrole-linked mono-and bis(1,3,4-oxadiazole) hybrids, attached to various arene units, was prepared using a two-step tandem protocol. Therefore, a benzohydrazide derivative was condensed with the appropriate aldehydes in ethanol at 80°C for 60-150 min to give the corresponding N-(benzoylhydrazones). Without isolation, the previous intermediates underwent intramolecular oxidative cyclization in dimethyl sulfoxide at 180°C for 90-200 min in the presence of chloramine trihydrate to afford the target hybrids. The cytotoxicity of all hybrids was examined in vitro against the MCF-7, HEPG2, and Caco2 cell lines. Arene-linked hybrids 4i and 4j, attached to p-nitro and pacetoxy units, were the most potent ones, with IC 50 values ranging from 5.47 to 8.80 and 12.75 to 21.22 μM, respectively, when tested on the above cell lines. At the tested concentrations of 5 and 7.5 μM, hybrid 4i inhibited thymidylate synthase (TS) with the best inhibition percentages of 72.3 and 91.3, whereas hybrid 4j displayed comparable inhibitory activity to the reference pemetrexed. Hybrid 4j had inhibition percentages of 62.7 and 82.6, whereas pemetrexed had inhibition percentages of 59.2 and 80.2, respectively. The capability of hybrids 4i and 4j as potential TS inhibitors is supported by molecular docking studies, while SwissADME predicts their efficacy as drug-like scaffolds.

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“…This was proven by 1 H NMR shifts for protons of the -COCH 3 group (1.21-2.30 ppm), as well as mass spectra where peaks of molecular ions were in accordance with acetylated compounds. Our attempt was to synthesize 1,3,4-oxadiazoles from Schiff bases employing other protocols too, like grinding Schiff bases with molecular iodine, 24 or cyclization with chloramine T 21 or ceric ammonium nitrate. 27 However, although some authors describe them as very effective procedures, they were not suitable for our type of compounds.…”

Section: Resultsmentioning

confidence: 99%

“…13 Khan and Akhtar 13 performed a synthesis of oxadiazoles from acylhydrazide using cyanogen bromide, while Sharba et al 14 reacted * Correspondence: maja.molnar@ptfos.hr N -formyl acid hydrazide with phosphorous pentasulfide to obtain a 1,3,4-oxadiazole ring. A well-known and often employed procedure for their preparation is the cyclization of Schiff bases in excess of acetic anhydride 15−19 in the presence of chloramine T 13,20,21 or ceric ammonium nitrate (CAN). 22 Aside from conventional methods in their preparation, ultrasound irradiation 23 or one-pot reaction of aromatic hydrazides with aryl aldehydes in the presence of catalytic amount of molecular iodine can be employed by grinding technique.…”

Section: Introductionmentioning

confidence: 99%

“…A well-known and often employed procedure for their preparation is the cyclization of Schiff bases in excess of acetic anhydride 15−19 in the presence of chloramine T 13,20,21 or ceric ammonium nitrate (CAN). 22 Aside from conventional methods in their preparation, ultrasound irradiation 23 or one-pot reaction of aromatic hydrazides with aryl aldehydes in the presence of catalytic amount of molecular iodine can be employed by grinding technique.…”

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confidence: 99%

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Biological study on novel coumarinyl 1,3,4-oxadiazoles

Molnar¹,

Amić²,

Pavić³

et al. 2018

Turk J Chem

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Coumarinyl 1,3,4-oxadiazoles were synthesized from Schiff bases and acetic anhydride. All compounds were characterized by melting points and their structures confirmed by mass and 1 H and 13 C NMR spectrometry.These novel coumarinyl derivatives were subjected to antibacterial, antifungal, antaflatoxigenic, and antioxidant activity.Their activity varied depending on their structure, where 2-(3-acetyl-5-(((4-methyl-2-oxo-2 H -chromen-7-yl)oxy)methyl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-1,4-phenylene diacetate showed significant antioxidant and antibacterial activity on B.subtilis. 4-(3-Acetyl-5-(((4-methyl-2-oxo-2 H -chromen-7-yl)oxy)methyl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-1,2-phenylene diacetate was found to possess excellent antifungal and antiaflatoxigenic activity.

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An efficient synthesis of ferrocenyl-containing 1,3,4-oxadiazole derivatives via oxidative cyclization reaction

Cited by 10 publications

References 19 publications

A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Biological study on novel coumarinyl 1,3,4-oxadiazoles

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