- Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
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Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi
- Kang, Ki-Tae,Park, Sang Hyun,Ryu, Do Hyun
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supporting information
p. 6679 - 6683
(2019/09/12)
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- N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles
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N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.
- Zhou, Quan,Liu, Shu,Ma, Ming,Cui, He-Zhen,Hong, Xi,Huang, Shuang,Zhang, Jing-Fan,Hou, Xiu-Feng
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p. 1315 - 1322
(2018/03/10)
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- Design, Synthesis, and Biological Activity of New N -(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension
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Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.
- Le Hiress, Morane,Akagah, Bernardin,Bernadat, Guillaume,Tu, Ly,Thuillet, Rapha?l,Huertas, Alice,Phan, Carole,Fadel, Elie,Simonneau, Gérald,Humbert, Marc,Jalce, Ga?l,Guignabert, Christophe
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p. 2725 - 2736
(2018/04/23)
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- Unexpected Decarboxylation-Triggered o-Hydroxyl-Controlled Redox Condensation of Phenylglycines with 2-Nitrophenols in Aqueous Media
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A decarboxylation-triggered and o-hydroxyl-controlled hydrogen-transfer strategy for the one-pot synthesis of benzoxazoles from readily available amino acids and 2-nitrophenols is reported. On the basis of this autoredox reaction, the C?N bond can be efficiently constructed to afford the desired products in moderate to good yields under transition-metal-free conditions in aqueous media. (Figure presented.).
- Tang, Lin,Yang, Zhen,Sun, Tian,Zhang, Di,Ma, Xiantao,Rao, Weihao,Zhou, Yuqiang
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p. 3055 - 3062
(2018/08/01)
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- Aryl schiff base derivate and preparation method and application thereof
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The invention discloses an aryl schiff base derivate and preparation method and a preparation method and application thereof. The structural formula of the aryl schiff base derivate sees description. The preparation method is characterized in that a certa
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Paragraph 0026; 0027; 0028; 0029; 0030; 0031-0038
(2017/08/28)
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- OMS-2/H2O2/Dimethyl Carbonate: An Environmentally-Friendly Heterogeneous Catalytic System for the Oxidative Synthesis of Benzoxazoles at Room Temperature
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A manganese octahedral molecular sieve (OMS-2) was found to be an efficient and recyclable heterogeneous catalyst for the oxidative synthesis of benzoxazoles in the gram-scale from phenolic imines at room temperature. H2O2 and biobased reagent dimethyl carbonate (DMC) were successfully employed as the environmentally friendly oxidant and solvent, respectively, in an OMS-2-catalysted redox reaction for the first time. Benzoxazoles could also be obtained from N-substituted 2-aminophenols via Cu(OH)x/OMS-2-catalyzed sequential oxidative transformation at elevated temperatures.
- Meng, Xu,Wang, Yuanguang,Chen, Baohua,Chen, Gexin,Jing, Zhenqiang,Zhao, Peiqing
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supporting information
p. 2018 - 2024
(2017/12/26)
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- Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation
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Highly efficient synthesis of benzofused heteroaromatic compounds via aerobic oxidation catalyzed by cyanide anion has been developed. The Schiff bases derived from 2-aminophenol and aldehydes provided the corresponding benzoxazoles in high yields in the presence of a catalytic amount of cyanide in an open flask under ambient conditions without the use of any external metal co-oxidants and bases. Furthermore, we have developed a catalytic sequential one-step protocol for the synthesis of benzoxazoles by adding a catalytic amount of NaCN to Schiff bases generated in situ from 2-aminophenol and aldehydes without the isolation of imine intermediates. This one-pot protocol was further extended to the synthesis of benzothiazoles from 2-aminothiophenol and aldehydes. A variety of aldehydes could be applied to this sequential one-pot protocol and the desired benzofused azole products were obtained in high yields.
- Cho, Yeon-Ho,Lee, Chun-Young,Cheon, Cheol-Hong
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p. 6565 - 6573
(2013/07/26)
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- Cyanide as a powerful catalyst for facile preparation of 2-substituted benzoxazoles via aerobic oxidation
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A cyanide-catalyzed synthesis of 2-substituted benzoxazoles from Schiff bases via aerobic oxidation has been developed. The products from various Schiff bases were obtained in high yields in an open flask under ambient conditions without other external oxidants. We have also developed a simple one-step protocol for the synthesis of benzoxazoles from aminophenol and the corresponding aldehydes in the presence of cyanide without isolation of imine intermediates. Copyright
- Cho, Yeon Ho,Lee, Chun-Young,Ha, Deok-Chan,Cheon, Cheol-Hong
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supporting information
p. 2992 - 2996
(2013/01/15)
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- Facile preparation of 2-substituted benzoxazoles and benzothiazoles via aerobic oxidation of phenolic and thiophenolic imines catalyzed by polymer-incarcerated platinum nanoclusters
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Platinum nanoclusters supported on a polymer/carbon black composite material was found to be an excellent catalyst for the oxidative cyclization of phenolic and thiophenolic Schiff bases to 2-substituted benzoxazoles and benzothiazoles under ambient conditions. Copyright
- Yoo, Woo-Jin,Yuan, Hao,Miyamura, Hiroyuki,Kobayashi, Shu
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supporting information; experimental part
p. 3085 - 3089
(2012/01/02)
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- Selective alkylation of aminophenols
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O-or N-Alkylated derivatives of aminophenols are important synthetic intermediates in organic synthesis. A series of aminophenols were selectively alkylated on their hydroxyl group in good yields via benzaldehyde protection of the amino group, subsequent alkylation, and hydrolysis; or on their amino group via imination and following reduction. ARKAT USA, Inc.
- Wang, Renchao,Xu, Jiaxi
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experimental part
p. 293 - 299
(2010/10/02)
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- Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases - A solution-phase strategy for library synthesis
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The Schiff base derived from the condensation of o-aminophenol with benzaldehydes was induced to undergo oxidative cyclization in the presence of DDQ. The resulting 2-arylbenzoxazoles were separated from the reduced DDQ by product by treatment of reaction mixture with a strongly basic ion-exchange resin. The applicability of this chemistry to spatially separate library synthesis is demonstrated by the preparation of a 352-member library.
- Chang, Junbiao,Zhao, Kang,Pan, Shifeng
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p. 951 - 954
(2007/10/03)
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- Synthesis of novel bis(benzoxazole) derivatives by tandem Claisen rearrangement and their fluorescence behavior
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Novel bis(benzoxazole) derivatives were easily synthesized from isobutenyl bis(amide-ether)s by tandem Claisen rearrangement and subsequent intramolecular cyclization of the amide-phenol intermediates. The yields of the bis(benzoxazole)s depended on wheth
- Koyama, Emiko,Yang, Gang,Tsuzuki, Seiji,Hiratani, Kazuhisa
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p. 1996 - 2006
(2007/10/03)
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- Synthesis of macrocyclic bis(phenylbenzoxazole) derivatives via tandem Claisen rearrangement and their fluorescence behavior
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Novel macrocyclic bis(phenylbenzoxazole) derivatives were easily synthesized from macrocyclic isobutenyl bis(amide-ether)s by tandem Claisen rearrangement and subsequent intramolecular cyclization of the amide-phenol intermediates. The position of substitution of the oligoethylene glycol moiety on the phenylamido groups of the macrocycles did not have a large effect on the yields of the bis(benzoxazole)s for the meta and para derivatives. The fluorescence quantum yields of most of the macrocyclic bis(benzoxazole)s were lower than those of the corresponding nonmacrocyclic bis(benzoxazole) model compounds. The quantum yields of the para-substituted macrocyclic bis(benzoxazole)s were clearly lower than those of the model compounds and decreased with increasing length of the oligoethylene chain.
- Koyama, Emiko,Tokuhisa, Hideo,Nagawa, Yoshinobu,Yang, Gang,Hiratani, Kazuhisa
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p. 1353 - 1360
(2007/10/03)
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