School of Pharmacy and Institutes of Biomedical Sciences , Fudan University , 826 Zhangheng Road , Shanghai 201203 , China.
Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
J Org Chem. 2019 Jan 18;84(2):914-923. doi: 10.1021/acs.joc.8b02795. Epub 2019 Jan 3.
An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2- c][1,3]oxazin-1-ones has been developed through a nucleophilic addition-cyclization process of N, O-acetal with ynamides. A number of substituted ynamides 8a-8o and 3-silyloxypyrrolidine or piperidine N, O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a-9o, 10a-10m were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, chiral ynamides 14a-14f could also experience this addition-cyclization process to afford products 15a-15f in excellent yields.
一种高效的不对称方法已经被开发出来，用于通过 N，O-缩醛与炔酰胺的亲核加成-环化过程来获得功能化的吡啶并[1,2-c][1,3]恶嗪-1-酮。许多取代的炔酰胺 8a-8o 和 3-硅氧基吡咯烷或哌啶 N，O-缩醛 6a、7 都适合这种转化，所需的产物 9a-9o、10a-10m 具有优异的区域选择性和突出的非对映选择性。此外，手性炔酰胺 14a-14f 也可以经历这种加成-环化过程，以优异的收率得到产物 15a-15f。
