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One-pot synthesis of 1,3-oxazin-4-ones through an Ir-catalyzed mild formal condensation reaction of secondary amides with acyl chlorides†
Si-Jia Yu,Jie Li,Jian-Liang Ye,Pei-Qiang Huang
Organic Chemistry Frontiers Pub Date : 03/06/2023 00:00:00 , DOI:10.1039/D3QO00092C
Abstract

A facile and efficient synthesis of bicyclic 1,3-oxazin-4-ones, 2,3,6,7-tetrahydrocyclopenta[e]-1,3-oxazin-4-ones and 2,3,5,6,7,8-hexahydro-4H-benzo[e]-1,3-oxazin-4-ones, has been achieved via an Ir-catalyzed one-pot reaction of secondary amides with adipoyl chloride and pimeloyl chloride, respectively. This method features good yields, broad substrate scope, mild reaction conditions, and scalability. This reaction also shows good compatibility with acetyl chloride and phenylacetyl chloride to access monocyclic 1,3-oxazin-4-ones.

Graphical abstract: One-pot synthesis of 1,3-oxazin-4-ones through an Ir-catalyzed mild formal condensation reaction of secondary amides with acyl chlorides
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