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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Traceless solid-phase synthesis of heteroannulated 1,3-oxazin-6-ones
Jun Che1, Makam S Raghavendra, Yulin Lam
1Department of Chemistry, National University of Singapore, Singapore.
Abstract:
A microwave-assisted solid-phase synthesis of heteroannulated 1,3-oxazin-6-ones has been developed. Significant rate enhancement was observed for all steps carried out under microwave irradiation, and the overall reaction time was dramatically shortened when compared to the conventional procedures. A representative set of 20 bi- and tricyclic heteroannulated 1,3-oxazin-6-ones was prepared. Key steps in the synthesis are (i) five-member heterocycle formation, (ii) acylation of amine, and (iii) ring closure to give the heteroannulated 1,3-oxazin-6-one.
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