- N-benzyl-benzoxazolone compound and synthesis method thereof
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The invention provides an N-benzyl-benzoxazolone compound and a synthesis method thereof. Under the condition of sealed air, catalyzed without metal, a benzoxazolone compound directly reacts with a methylbenzene compound to prepare the N-benzyl-benzoxazolone compound. Compared with the prior art, the synthesis method is very simple and convenient, raw materials are easy to obtain, the cost is low, the efficiency is high, the method is suitable for various reaction substrates. Prepared products can be used for clinical drugs and drug intermediates capable of effectively treating diseases.
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Paragraph 0055-0060
(2017/10/07)
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- Synthesis of 3-alkylbenzoxazolones from N-alkyl-N-arylhydroxylamines by contiguous O-trichloroacetylation, trichloroacetoxy ortho-shift, and cyclization sequence
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Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N→Cortho trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.
- Ram, Ram N.,Soni, Vineet Kumar
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p. 11935 - 11947
(2014/01/06)
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- Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF)
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The cytokine MIF is involved in inflammation and cell proliferation via pathways initiated by its binding to the transmembrane receptor CD74. MIF also exhibits keto-enol tautomerase activity, believed to be vestigial in mammals. Starting from a 1 μM hit from virtual screening, substituted benzoxazol-2-ones have been discovered as antagonists with IC50 values as low as 7.5 nM in a tautomerase assay and 80 nM in a MIF-CD74 binding assay. Additional studies for one of the potent inhibitors demonstrated that it is not a covalent inhibitor of MIF and that it attenuates MIF-dependent ERK1/2 phosphorylation in human synovial fibroblasts.
- Hare, Alissa A.,Leng, Lin,Gandavadi, Sunilkumar,Du, Xin,Cournia, Zoe,Bucala, Richard,Jorgensen, William L.
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scheme or table
p. 5811 - 5814
(2010/12/20)
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- DABCO- and DBU-accelerated green chemistry for N-, O-, and S-benzylation with dibenzyl carbonate
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An environmentally friendly process for the benzylation of nitrogen, oxygen, or sulfur atoms with dibenzyl carbonate has been developed. Catalytic amounts of DABCO or DBU can accelerate this 'green' alkylation.
- Shieh, Wen-Chung,Lozanov, Mario,Loo, Mauricio,Repi?, Oljan,Blacklock, Thomas J.
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p. 4563 - 4565
(2007/10/03)
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- The Reaction of Dialkyl Carbonates with o-Aminophenol Catalysed by K 2CO3: A Novel High-Yield Synthesis of N-Alkylbenzoxazol-2- ones
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At 130-150°C and in the presence of catalytic K2CO 3, o-aminophenol (1) readily reacts with dialkyl carbonates (2: ROCO2R; 2a: R = Me, 2b: Et, 2c: Allyl, 2d: Bn) to give the corresponding N-alkylbenzoxazol-2-ones (3a-d) in high yields (88-98%). This reaction is a rare example where dialkyl carbonates may simultaneously act as carbonylating and alkylating agents likely through a BAc2/B A12 sequence. Moreover, compounds 2a-c serve also as solvents. In the case of 2d, 1,2-dimethoxyethane (DME) is the reaction medium.
- Selva, Maurizio
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p. 2872 - 2876
(2007/10/03)
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- Unsymmetrical Diarylketones from Electron-rich Heterocyclic Arenes
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AlCl3-mediated chlorocarbonylation of a first arene by oxalyl chloride followed by in situ Friedel-Crafts acylation of a second electron-rich arene expeditiously provides, in a one-pot procedure, either symmetrical or unsymmetrical benzophenones with yields ranging from 17-52%. Best results are obtained when the more activated substrate is used as the second arene. Another advantage is that the resultant benzophenone precipitates from the reaction mixture allowing facile workup.
- Poupaert, Jacques H.,Depreux, Patrick,McCurdy, Christopher R.
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p. 823 - 830
(2007/10/03)
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- Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)- benzothiazolone derivatives
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A series of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives were synthesized and evaluated for anticonvulsant activity. The compounds were assayed, intraperitoneally in mice and per os in rats, against seizures induced by maximal electroshock (MES) and pentylene-tetrazole (scMet). Neurologic deficity was evaluated by the rotarod test. The compounds were prepared to determine the relationship between the 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives' structures and anticonvulsant activity. Several of these compounds showed significant anticonvulsant activity. Compounds 43 and 45 were the most active of the series against MES-induced seizures with ED50 values of 8.7 and 7.6 mg/kg, respectively. Compound 45 displayed good protection against MES-induced seizures and low toxicity in rats with an oral ED50 of 18.6 mg/kg and a protective index (PI = TD50/ED50) of 1 receptors with nanomolar affinities.
- Ucar, Huseyin,Van Derpoorten, Kim,Cacciaguerra, Silvia,Spampinato, Santi,Stables, James P.,Depovere, Paul,Isa, Majed,Masereel, Bernard,Delarge, Jacques,Poupaert, Jacques H.
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p. 1138 - 1145
(2007/10/03)
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- AlCl3-DMF reagent in the friedel-crafts reaction. Application to the synthesis of symmetrical benzophenone derivatives
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Synthesis of series of symmetrical benzophenone derivatives by C-alkylation reaction of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone with carbon tetrachloride in presence of AlCl3-DMF reagent is reported.
- Ucar, Huseyin,Van Derpoorten, Kim,Poupaert, Jacques H.
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p. 805 - 810
(2007/10/03)
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- Synthesis of 3-Substitued Benzoxazoline-2-thiones
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Several methods for the preparation of 3-substitued benzoxazoline-2-hiones (1) were examined.Method B via the thiation of 3-substitued benzoxazoline-2-one (5) with phosphorus pentasulfide was found to be applicable to the preparation of most analogs of 1, with a few expections.Method C via the cyclization of 2-(alkylamino)phenol (7) with potassium O-methyldithiocarbonate was suitable for the preparation of analogs with a group sensitive to high temperature of with an aryl- (including aromatic heterocyclic ring) methyl group.In addition, the reaction of benzoxazoline-2-thione (2) with acetals such as 1-ethoxyisochroman, 2-ethoxytetrahydrofuran, and ethoxytetraydropyran, or with Michael acceptors such as 2,3-dihydrofuran and 2H-3,4-dihydropyran, gave 3-substitued benzoxazoline-2-thione (1d-f).
- Yamato, Masatoshi,Takeuchi, Yasuo,Hashigaki, Kuniko,Hattori, Kyoko,Muroga, Eiko,Hirota, Takashi
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p. 1733 - 1737
(2007/10/02)
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