Reactions of 6-[bis(trimethylsilyl)amino]-5,6-dihydro-4H-1,2-oxazines

✍ Scribed by Paulini, Klaus ;Gerold, Andreas ;Reißig, Hans-Ulrich

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 513 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199519950494

✦ Synopsis

1 ,ZOxazines, bis(trimethylsily1)amino-substituted / Hydrogenolysis / Deprotonation / Alkylation / Deuteration 1,2-Oxazine 1 was converted into an unusual condensation product 5 by treatment with tetra-n-butylammonium fluoride. The hydrogenolysis of 1 with Pd/C as catalyst provided the expected primary amine 9, whereas the same reaction with the ethoxycarbonyl-substituted 1,2-oxazine 2 as starting material gave the 4-methylproline derivative 10 after N-protection. Deprotonation at C-4 of 1 required rather harsh con-We recently described[*] the smooth synthesis of 6-[bis-(trimethylsilyl)amino]-substituted 5,6-dihydro-4H-l,2-oxazines 1-3. The highly diastereoselective bromination of 1 and 2 allowed the preparation of additional 4-substituted derivatived31. In this paper we present our experiments concerning other reactions of 1-3 and we compare these with related transformations of 6-trimethylsiloxy-substituted 1,2-0xazines.