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Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-α-pyronen), 15.Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornadien. Ein neuer Weg zu 3,6-disubstituierten α-Pyronen

✍ Scribed by Christl, Manfred ;Bodenschatz, Gabriele ;Feineis, Erich ;Hegmann, Joachim ;Hüttner, Gerhard ;Mertelmeyer, Stefan ;Schätzlein, Klaus

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Cycloadditions of 6__H__‐1,2,4‐Oxadiazin‐6‐ones (4,5‐Diaza‐α‐pyrones), 15.Part 14: Ref.^[1]^.

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Reactions of 6__H__‐1,3,4‐Oxadiazin‐6‐ones with Norbornadiene. A New Route to 3,6‐Disubstituted α‐Pyrones

Upon reaction with norbornadiene, ten disubstituted 1,3,4‐oxadiazin‐6‐ones 1 were converted into 3,6‐disubstituted α‐pyrones 6. For this purpose, solutions of the substrates were treated with boron trifluoride‐ether or trifluoroacetic acid. The smooth formation of 6 was also observed when a γ‐oxo ketene, initially generated by heating a solution of the substrates in the absence of boron trifluoride–ether, was allowed to react with the Lewis acid. Without use of an acid, only 6f could be obtained free from further compounds, whereas in the other cases enol lactones and 1:2 products of the types 8 and 7 were formed additionally. Oxadiazinone 1j gave enol lactone 10 in the noncatalysed reaction.

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