Issue 40, 2020

Efficient and stereoselective one-pot synthesis of benzo[b]oxazolo[3,4-d][1,4]oxazin-1-ones

Abstract

An efficient and mild one-pot convergent synthesis protocol has been developed for benzo[b]oxazolo[3,4-d][1,4]oxazin-1-one derivatives through the Mitsunobu reaction and sequential cyclization. Various tricyclic fused benzoxazinyl-oxazolidinones (20 examples) were obtained in good to excellent yields and high enantioselectivities with facile operation. Furthermore, four stereoisomers were afforded respectively in high ee values (>97.8%) via using different chiral 2,3-epoxy-4-trityloxybutanol. This methodology has been applied to the synthesis of key intermediates of drug candidates.

Graphical abstract: Efficient and stereoselective one-pot synthesis of benzo[b]oxazolo[3,4-d][1,4]oxazin-1-ones

Supplementary files

Article information

Article type
Paper
Submitted
07 May 2020
Accepted
05 Jun 2020
First published
23 Jun 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 24037-24044

Efficient and stereoselective one-pot synthesis of benzo[b]oxazolo[3,4-d][1,4]oxazin-1-ones

H. Zhao, W. Zhao, S. Cheng, H. Lu, D. Zhang and H. Huang, RSC Adv., 2020, 10, 24037 DOI: 10.1039/D0RA04104A

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