AgNTf2 catalyzed cycloaddition of N-acyliminium ions with alkynes for the synthesis of the 3,4-dihydro-1,3-oxazin-2-one skeleton

A catalyzed process for the synthesis of the 4,6-substituted 3,4-dihydro-1,3-oxazin-2-one skeleton has been developed through cycloaddition of in situ generated acyliminium intermediates with alkynes. A range of chain N,O-acetals and terminal alkynes were amenable for this mild transformation. As a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-06, Vol.20 (25), p.5086-5094
Main Authors: Wen-Ke, Xu, Jia-Ming, Guo, Chang-Hong, Liu, Jian-Ting, Sun, Lv, Min, Bang-Guo, Wei
Format: Article
Language:English
Subjects:
Acetals
Alkynes
Chemical synthesis
Cycloaddition
Intermediates
Online Access:Get full text
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Summary:A catalyzed process for the synthesis of the 4,6-substituted 3,4-dihydro-1,3-oxazin-2-one skeleton has been developed through cycloaddition of in situ generated acyliminium intermediates with alkynes. A range of chain N,O-acetals and terminal alkynes were amenable for this mild transformation. As a result, a series of desired cycloaddition products were obtained in moderate to good yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00900e