A novel approach towards the synthesis of an oxazine scaffold using scandium trifluoromethanesulfonate catalysed N, O-acetal and olefin cyclisation sequence

[Display omitted] A novel approach to [1,3]oxazin-1-ones from 1,1-disubstituted alkene and N,O-acetals through scandium trifluoromethanesulfonate as catalyst in dichloroethane at 60 °C. The structure of this product is easily accessible. This protocol merits several advantages, such as very gentle c...

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Bibliographic Details
Published inTetrahedron letters Vol. 125; pp. 154614 - 154617
Main Authors Yang, Tian-Yu, Yang, Xuan, Cheng, Yu, Gao, Xue-ting, Fu, Shu-Ming, Zhang, Tao, Du, Zhen-Ting
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.07.2023
Elsevier
Subjects
[1,3]oxazin-1-ones
Chemistry
Chemistry, Organic
Cyclization
N, O-acetal
Physical Sciences
Scandium trifluoromethanesulfonate
Science & Technology
[1,3]oxazin-1-ones
Cyclization
N, O-acetal
Scandium trifluoromethanesulfonate
1
O-acetal
3]oxazin-1-ones
CONTAINING HETEROCYCLIC-COMPOUNDS
N
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Summary:[Display omitted] A novel approach to [1,3]oxazin-1-ones from 1,1-disubstituted alkene and N,O-acetals through scandium trifluoromethanesulfonate as catalyst in dichloroethane at 60 °C. The structure of this product is easily accessible. This protocol merits several advantages, such as very gentle conditions, cheap starting materials, and high yields. Altogether, 22 cases were investigated, and all the products were confirmed by spectrum methods. Three compounds were performed single crystal diffraction. The diastereochemistry was also studied in several cases.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154614