Synthesis of N-(4,6-Dimethylpyridin-2-yl)benzoxazolinonyl Methylcarboxamides with Potential Antiinflammatory Activity

Liacha, Messaoud; Yous, Saı̈d; Depreux, Patrick; Poupaert, Jacques H.; Lesieur, D.

doi:10.3987/com-99-8572

Cited by 15 publications

(1 citation statement)

References 7 publications

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“…Yield = 976 mg (86%), pale brown needles, mp = 180–181°C (EtOH),/lit. mp = 183–185°C (toluene) [63], 1 H NMR (500 MHz, DMSO) δ 11.70 (s, 1H), 7.39 (s, 1H), 7.05 (s, 1H), 2.30 (s, 3H). 13 C NMR (126 MHz, DMSO) δ 154.32, 141.97, 130.79, 129.49, 125.63, 111.49, 110.17, 19.55.…”

Section: Methodsmentioning

confidence: 99%

Facile and environmentally benign synthetic approach to the selective mono‐chlorination and mono‐bromination of benzo[d]OXAZOL‐2(3H)‐ONES

Kurutos

Minkovska

Nedialkov

et al. 2022

Journal of Heterocyclic Chem

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Exhibiting a wide spectrum of practical applications, benzo[d]oxazol‐2(3H)‐ones (BOA) are considered as key intermediates in the synthesis of pharmaceutical products, organic dyes, and OLED materials among others. Herein, we propose an environmentally benign protocol for the selective mono‐halogenation of benzo[d]oxazol‐2(3H)‐ones. Several chloro‐ and bromo‐substituted BOA derivatives were prepared within less than an hour with high to excellent yields (75%–93%) via this novel, green, and energy sufficient method. This rapid and highly reproducible synthetic approach employs inexpensive commercially available urea‐hydrogen peroxide complex and hydrochloric or hydrobromic acid. Simple operations and precise control over the oxidative halogenation, with water being the major by‐product of the reaction outcome, are among the strong point of current facile method from the perspective of green chemistry.

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Section: Methodsmentioning

confidence: 99%

Facile and environmentally benign synthetic approach to the selective mono‐chlorination and mono‐bromination of benzo[d]OXAZOL‐2(3H)‐ONES

Kurutos

Minkovska

Nedialkov

et al. 2022

Journal of Heterocyclic Chem

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ChemInform Abstract: Synthesis of N‐(4,6‐Dimethylpyridin‐2‐yl)‐benzoxazolinonyl Methylcarboxamides with Potential Antiinflammatory Activity.

Liacha¹,

Yous²,

Depreux³

et al. 1999

ChemInform

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Selenium‐Catalyzed Reductive Carbonylation of 2‐Nitrophenols to2‐Benzoxazolones

et al. 2005

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2‐Benzoxazolones or 2‐benzimidazolones are synthesized in moderate to good yields in the presence of a base (KOH, NaOH, KOAc, NEt3, DBU) at atmospheric pressure or under a high pressure of CO by one‐pot reductive carbonylation of 2‐nitrophenols or 2‐nitroaniline in the presence of selenium as catalyst. Besides the effect of base, the effects of solvent and temperature on the reaction were investigated at high or atmospheric pressure. Contrasting results were obtained for 2‐benzoxazolones or 2‐benzimidazolone at high and atmospheric pressures. Moreover, phase‐transfer catalysis was exhibited. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

show abstract

Synthesis of N-(4,6-Dimethylpyridin-2-yl)benzoxazolinonyl Methylcarboxamides with Potential Antiinflammatory Activity

Cited by 15 publications

References 7 publications

Facile and environmentally benign synthetic approach to the selective mono‐chlorination and mono‐bromination of benzo[d]OXAZOL‐2(3H)‐ONES

Facile and environmentally benign synthetic approach to the selective mono‐chlorination and mono‐bromination of benzo[d]OXAZOL‐2(3H)‐ONES

ChemInform Abstract: Synthesis of N‐(4,6‐Dimethylpyridin‐2‐yl)‐benzoxazolinonyl Methylcarboxamides with Potential Antiinflammatory Activity.

Selenium‐Catalyzed Reductive Carbonylation of 2‐Nitrophenols to2‐Benzoxazolones

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