Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones

He Yun; Agarwal Piyush K.; Kiran I. N. Chaithanya; Yu Ruocheng; Cao Bei; Zou Cheng; Zhou Xinghua; Xu Huacheng; Xu Biao; Zhu Lei; Lan Yu; Nicolaou K. C.

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Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones

机译：由N取代的2-恶唑酮有效合成二聚恶唑，哌啶和四氢异喹啉

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A mild and practical method for the construction of heterocycles from N-substituted 2-oxazolones through cascade, BF3 center dot Et2O/H2O-catalyzed reactions involving iminium ion generation and trapping by external or internal olefinic and aryl moieties is described. Mechanistic and computational studies revealed the strong protic acid HBF4 as the initiating catalyst for these cascade reactions. Providing access to novel molecular diversity, these processes may facilitate chemical biology studies, drug discovery efforts and natural products synthesis.

机译：描述了一种温和而实用的方法，用于通过N-取代的2-恶唑酮通过级联的BF3中心点Et2O / H2O催化的反应（包括亚胺离子的产生以及外部或内部烯烃和芳基部分的捕获）来构建杂环。机理和计算研究表明，强质子酸HBF4是这些级联反应的引发催化剂。这些过程提供了获得新颖分子多样性的途径，可以促进化学生物学研究，药物发现工作和天然产物合成。

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《Chemistry: A European journal》 |2016年第23期|共6页
作者
He Yun; Agarwal Piyush K.; Kiran I. N. Chaithanya; Yu Ruocheng; Cao Bei; Zou Cheng; Zhou Xinghua; Xu Huacheng; Xu Biao; Zhu Lei; Lan Yu; Nicolaou K. C.;
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正文语种 eng
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关键词
cascade reactions; cyclization; heterocycles; molecular diversity; 2-oxazolones;

机译：级联反应;环化;杂环;分子多样性;2-恶唑酮;

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1. Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones [J] . He Yun, Agarwal Piyush K., Kiran I. N. Chaithanya, Chemistry: A European journal . 2016,第23期

机译：由N取代的2-恶唑酮有效合成二聚恶唑，哌啶和四氢异喹啉
2. Synthesis of N-substituted 4-(4-hydroxyphenyl)piperidines, 4-(4-hydroxybenzyl)piperidines, and (+/-)-3-(4-hydroxyphenyl)pyrrolidines: selective antagonists at the 1A/2B NMDA receptor subtype. [J] . Guzikowski AP, Tamiz AP, Acosta Burruel-M, Journal of Medicinal Chemistry . 2000,第5期

机译：N-取代的4-（4-羟苯基）哌啶，4-（4-羟苄基）哌啶和（+/-）-3-（4-羟苯基）吡咯烷的合成：1A / 2B NMDA受体亚型的选择性拮抗剂。
3. A novel ring oxidation of 4- or 5-substituted 2H-oxazole to corresponding 2-oxazolone catalyzed by cytosolic aldehyde oxidase [J] . AroraV.K., PhilipT., HuangS., Drug Metabolism and Disposition: The Biological Fate of Chemicals . 2012,第9期

机译：胞质醛氧化酶催化4-或5-取代的2H-恶唑新型环氧化为相应的2-恶唑酮
4. FENTEPHALINES: DIMERIC BIOACTIVE PEPTIDES BASED ON AMINO ACIDS COUPLED TO 4-ANILINO-N-PHENETHYL-PIPERIDINE [C] . Ravil R. Petrov, Ruben S. Vardanyan, Yeon S. Lee the European Peptide Symposium . 2007

机译：Fentephalines：基于氨基酸的二聚体生物活性肽偶联至4-苯胺 - N-苯乙烯 - 哌啶
5. Asymmetric synthesis of pyrrolidines, piperidines, and tetrahydroisoquinolines utilizing enantiopure sulfinimines. [D] . Yang, Bin. 2008

机译：利用对映纯的亚磺胺类化合物不对称合成吡咯烷，哌啶和四氢异喹啉。
6. Solid-Phase Synthesis of N-Substituted Pyrrolidinone Tethered N-substituted Piperidines via Ugi Reaction [O] . Zhang Liu, Adel Nefzi -1

机译：通过Ugi反应的N-取代的吡咯烷酮系链固相合成的N-取代的哌啶
7. Frontispiece: Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N -Substituted 2-Oxazolones [O] . Yun He, Piyush K. Agarwal, I. N. Chaithanya Kiran, 2016

机译：正面：高效合成二聚体氧化的二恶唑，哌啶和四羟基异喹啉，来自N-溶液的2-恶唑酮

Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones

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