Direct synthesis of oxazolidin-2-ones from tert -butyl allylcarbamate via halo-induced cyclisation

Paisuwan, Waroton; Chantra, Thanakrit; Rashatasakhon, Paitoon; Sukwattanasinitt, Mongkol; Ajavakom, Anawat

doi:10.1016/j.tet.2017.04.063

Cited by 9 publications

(3 citation statements)

References 35 publications

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“…5‐(Hydroxymethyl)‐3‐(3‐methylphenyl)oxazolidin‐2‐one (toloxatone) (2 r) : Analytical TLC on silica gel, 3:2 EtOAc/petroleum ether, R f =0.09; white solid; yield 70 % (72 mg); m.p. : 78–79 °C (lit .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Oxazolidinones by using Carbon Dioxide as a C₁ Building Block and an Aluminium‐Based Catalyst

2019

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Oxazolidinone synthesis through the coupling of carbon dioxide and aziridines was catalysed by an aluminium(salphen) complex at 50–100 °C and 1–10 bar pressure under solvent‐free conditions. The process was applicable to a variety of substituted aziridines, giving products with high regioselectivity. It involved the use of a sustainable and reusable aluminium‐based catalyst, used carbon dioxide as a C1 source and provided access to pharmaceutically important oxazolidinones as illustrated by a total synthesis of toloxatone. This protocol was scalable, and the catalyst could be recovered and reused. A catalytic cycle was proposed based on stereochemical, kinetic and Hammett studies.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Oxazolidinones by using Carbon Dioxide as a C₁ Building Block and an Aluminium‐Based Catalyst

2019

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“…These derivatives exhibit a range of valuable activities comprising anti-cancer, anti-inflammatory, antipyretic, anticonvulsant, antifungal, antimicrobial, anthelmintic, antianxiety, and anti-depressive effects, as well as acting as HIV-1 inhibitors. Their versatility makes them critical assets in pharmaceutical drug design 34 , 35 .…”

Section: Introductionmentioning

confidence: 99%

Phosphomolybdic acid supported on magnetic poly calix[4]resorcinarene-EDTA-chitosan network as a recyclable catalyst for the synthesis of 5-aroyl-NH-1,3-oxazolidine-2-ones

Moradi,

Mozafari,

Ghadermazi

2024

Sci Rep

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In this work, a novel procedure for immobilization of phosphomolybdic acid (PMA) on Magnetic polycalix[4]resorcinarene grafted to chitosan by EDTA (calix-EDTA-Cs) was reported. The heterogeneous nanocomposite (CoFe2O4@calix-EDTA-Cs@PMA) was applied an acid nanocatalyst for the synthesis of 5-aroyl-NH-1,3-oxazolidine-2-ones through the reaction of α-epoxyketones with sodium cyanate (NaOCN) in polyethylene glycol (PEG) as a green solvent under ultrasonic irradiation conditions. Some features of this work include quick reaction time, high reaction yield, easy separation of the catalyst, thermal stability, and eco-friendly.

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“…In 2017, Paisuwan et al developed a simple methodology for construction of the 2-oxazolidinone derivatives (13aX and 13bX). We also successfully synthesized toloxatone drug (Humoryl ® ) by utilizing developed method through halo-induced cyclisation of tert-butyl allyl(phenyl)carbamate 12 by using various halogenating reagents [44]. Practically, cyclisation reaction to yield 13aX prefers the relatively less reactive halonium ionic species (NCS, NBS, NIS, and I 2 ), on the other hand, the relatively more reactive halonium ion (Cl 2 , Br 2 , KI/KIO 3 ) tend to perform through both cyclisation reaction and S E Ar furnishing dihalo-substituted-2-oxazolidinone 13bX in…”

Section: Oxazolidinone Synthesismentioning

confidence: 99%

Synthesis and development of dipicolylamine derivatives as new fluorescent chemosensors

Paisuwan

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Di-2-picolylamine (DPA)?is a powerful chelator for many transition metal ions. In this thesis, new DPA fluorescent chemosensors consisting of a fluorophore such as either naphthalimide or quinoline are developed. The first part?deals with the synthesis of?1,8-naphthalimide derivatives linked 2-, 3-, 4-((bis(pyridin-2-ylmethyl)amino)methyl)aniline, and 4-amino-2-((bis(pyridin-2-ylmethyl)amino)methyl)phenol. The metal ion sensing experiments showed?N3D was selective toward Ag+ with fluorescent enhancement in aqueous emitting green fluorescence under blacklight. The complexation of [N3D+Ag+] is?a 1:1 stoichiometric binding with?a limit of detection (LOD) 0.67 ?M. Second part is the synthesis of oxazolidinonyl DPA?derivatives by using self-developed halo-induced cyclization followed by substitution. 6QOD displayed a remarkable fluorescent enhancement in aqueous media with the presensce of Hg2+?and?in CH3CN with the presensce of Fe3+ showing?LOD 1.01 and 0.22 ?M, respectively. The fluorescent color of both cases changed into green. The probe recognized Hg2+ or Fe3+ ions based on a 1:1 complexation. From the 1H NMR investigation, the probe binds with?Hg2+?and?Fe3+?as tetradentate and tridentate ligand, respectively. The sensing mechanism probably involves the inhibition of photoinduced electron transfer between DPA unit and quinoline. Furthermore, we also synthesized QAD derivatives that the linker of QOD derivatives was changed from oxazolidinone to acetamide in order to compare the sensing property in term of rigidity of the linker. 6QAD is?selective toward?both metal ions in the same manner as of 6QOD but with lower sensitivities.

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Direct synthesis of oxazolidin-2-ones from tert -butyl allylcarbamate via halo-induced cyclisation

Cited by 9 publications

References 35 publications

Synthesis of Oxazolidinones by using Carbon Dioxide as a C₁ Building Block and an Aluminium‐Based Catalyst

Synthesis of Oxazolidinones by using Carbon Dioxide as a C₁ Building Block and an Aluminium‐Based Catalyst

Phosphomolybdic acid supported on magnetic poly calix[4]resorcinarene-EDTA-chitosan network as a recyclable catalyst for the synthesis of 5-aroyl-NH-1,3-oxazolidine-2-ones

Synthesis and development of dipicolylamine derivatives as new fluorescent chemosensors

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Direct synthesis of oxazolidin-2-ones from tert -butyl allylcarbamate via halo-induced cyclisation

Cited by 9 publications

References 35 publications

Synthesis of Oxazolidinones by using Carbon Dioxide as a C1 Building Block and an Aluminium‐Based Catalyst

Synthesis of Oxazolidinones by using Carbon Dioxide as a C1 Building Block and an Aluminium‐Based Catalyst

Phosphomolybdic acid supported on magnetic poly calix[4]resorcinarene-EDTA-chitosan network as a recyclable catalyst for the synthesis of 5-aroyl-NH-1,3-oxazolidine-2-ones

Synthesis and development of dipicolylamine derivatives as new fluorescent chemosensors

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Synthesis of Oxazolidinones by using Carbon Dioxide as a C₁ Building Block and an Aluminium‐Based Catalyst

Synthesis of Oxazolidinones by using Carbon Dioxide as a C₁ Building Block and an Aluminium‐Based Catalyst