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通过氮杂氧杂烯丙基正离子与两性化合物的[3 + 3]-和[3 + 4]-环加成反应一步合成功能化的吗啉酮和 1,4-噁嗪烷-3-酮。

One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- and [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds.

机构信息

Division of Molecular Synthesis & Drug Discovery , Centre of Biomedical Research (CBMR) , SGPGIMS Campus. Raebareli Road , Lucknow 226014 , Uttar Pradesh , India.

Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling (ACMM) , Vrije Universiteit Amsterdam , De Boelelaan 1083 , Amsterdam 1081 HV , The Netherlands.

出版信息

J Org Chem. 2019 Dec 6;84(23):15255-15266. doi: 10.1021/acs.joc.9b02269. Epub 2019 Nov 21.

Abstract

A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,]-amphoteric compounds ( = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a π-electrophilic site.

摘要

提出了一种新的[3 + 3]-和[3 + 4]-环化策略,涉及氮杂氧杂戊烯阳离子和[1,]-两性化合物(= 3,4)。这种简洁的方法能够轻松组装功能化的饱和 N-杂环,由六元和七元环组成,在药物发现方法中具有重要意义。该反应还代表了氮杂氧杂戊烯阳离子与不同链长的两性试剂之间的新捕获模式,这些试剂由一个杂原子亲核位点和一个π-亲电位点组成。

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