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Reductive Transformations of 6H-1,2-Oxazines with Hydride Reagents: Formation of Aziridines and 3-Hydroxyalkylated 1,2-oxazines

✍ Scribed by Zimmer, Reinhold ;Homann, Kai ;Reißig, Hans-Ulrich

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 299 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1993199301186

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✦ Synopsis

Abstract

6__H__‐1,2‐Oxazines 1 and 3 are converted into aziridines 2 and 4, respectively, by reduction with LiAlH~4~. Reduction of 1,2‐oxazine 5 lacking the 6‐alkoxy substituent leads to phenyl ketone 6, 6‐Alkoxy‐substituted 1,2‐oxazine‐3‐carboxylates 7, 9, and 11 are reduced with NaBH~4~ to give the corresponding 3‐hydroxymethylated compounds 8, 10, and 12 in good yields.

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