- Metal-free iodine(iii)-promoted synthesis of 2,5-diaryloxazoles
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A nonmetal-catalyzed oxidative cyclization to achieve 2,5-disubstituted oxazoles from inexpensive and readily available substituted chalcone, (diacetoxyiodo)benzene (PIDA) and ammonium acetate (NH4OAc) at room temperature is described. The reaction forms a variety of 2,5-diaryloxazoles in good to excellent yields with broad substrate scope under mild conditions without the requirement of ligands and additional bases.
- Yang, Xueying,Guo, Xin,Qin, Mingda,Yuan, Xinglong,Jing, Huanwang,Chen, Baohua
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supporting information
p. 3104 - 3108
(2018/05/22)
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- Synthesis of 2,5-disubstituted oxazoles: Via cobalt(III)-catalyzed cross-coupling of N -pivaloyloxyamides and alkynes
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An efficient synthesis of 2,5-disubstituted oxazoles via Co(iii) catalysis is described herein. The synthesis is achieved under mild conditions through [3+2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated via this protocol.
- Yu, Xiaolong,Chen, Kehao,Wang, Qi,Zhang, Wenjing,Zhu, Jin
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supporting information
p. 1197 - 1200
(2018/02/09)
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- N -Bromosuccinimide as a Brominating Agent for the Transformation of N -H (or N -Benzyl) Ketoaziridines into Oxazoles
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A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.
- Samimi, Heshmat A.,Dadvar, Farkhondeh
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p. 1899 - 1904
(2015/06/30)
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- Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides
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Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.
- Samanta, Supravat,Donthiri, Ramachandra Reddy,Dinda, Milan,Adimurthy, Subbarayappa
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p. 66718 - 66722
(2015/08/24)
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- Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
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An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.
- Gao, Qing-He,Fei, Zhuan,Zhu, Yan-Ping,Lian, Mi,Jia, Feng-Cheng,Liu, Mei-Cai,She, Neng-Fang,Wu, An-Xin
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- Convenient one-pot synthesis of 2,5-disubstituted oxazoles via a catalytic oxidative dehydrogenation of F3CSO3H·SiO 2-DDQ/CuCl2/LiCl
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A facile one-pot synthesis of 2,5-disubstituted oxazoles was developed via cyclization of aldoximes and phenylacetylene then dehydrogenation oxidation. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was studied for the selective oxidation of oxazolines using Cu2+/Li+ as catalyst and O2 as indirect oxidant. The reaction results showed that this catalyst system can effectively catalyze the oxidation of oxazolines to the corresponding oxazoles. Thus, a variety of polysubstituted oxazoles was easily synthesized in high yields by catalytic oxidation of 2,3-dichloro-5,6-dicyano-1, 4-benzoquinone/CuCl2/LiCl/O2.
- Yuan, Shizhen,Li, Zhen,Xu, Ling
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p. 1405 - 1409
(2014/01/06)
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- Iodine(III)-promoted synthesis of oxazoles through oxidative cyclization of N -styrylbenzamides
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The hypervalent iodine reagent PhI(OTf)2, generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction. Georg Thieme Verlag Stuttgart, New York.
- Hempel, Christian,Nachtsheim, Boris J.
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p. 2119 - 2123
(2013/10/21)
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- Simple and efficient preparation of 2,5-disubstituted oxazoles via a metal-free-catalyzed cascade cyclization
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A practical and simple synthesis of 2,5-disubstituted oxazoles was developed via an iodine-catalyzed tandem oxidative cyclization. A wide range of common commercial aromatic aldehydes can be used as reaction substrates, which displayed excellent functional group compatibility in this reaction.
- Wan, Changfeng,Gao, Linfeng,Wang, Qiang,Zhang, Jintang,Wang, Zhiyong
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supporting information; experimental part
p. 3902 - 3905
(2010/11/04)
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- TBHP/I2-mediated domino oxidative cyclization for one-pot synthesis of polysubstituted oxazoles
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A facile type of one-pot, transition-metal-free domino process was developed for the synthesis of oxazoles. Thus, a variety of polysubstituted oxazoles were easily synthesized via t-BuOOH/I2-mediated domino oxidative cyclization from readily available starting materials under mild conditions.
- Jiang, Huanfeng,Huang, Huawen,Cao, Hua,Qi, Chaorong
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supporting information; experimental part
p. 5561 - 5563
(2011/02/25)
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- 2,5-SUBSTITUTED OXAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS FOR THE TREATMENT OF CANCER
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Certain oxazole-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, methods of using compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions comprising compounds exhibiting ATP-utilizing enzyme inhibitory activity, are disclosed.
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Page/Page column 61; 64
(2010/11/29)
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