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3,4-Dihydro-6-methyl-1,2-benzoxathiin-2,2-dioxid-Derivate mit Enaminketon-Strukturen aus 6-Methyl-4-chromon-3-sulfonsäure-phenylester

✍ Scribed by Löwe, Werner ;Jeske, Peter

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
278 KB
Volume
1985
Category
Article
ISSN
0947-3440

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✦ Synopsis

Eingegangen am 8. Februar 1985 Primire und sckundare Amine reagieren rnit 6-Mcthyl-4-chromon-3-sulfonsaure-phenylester (5) unter Bildung von 3,4-Dihydro-6-methyl-1,2-benzoxathiin-2,2-dioxid-Derivaten 8a -g mit Enaminketon-Strukturen. Diese Ringtransformationsreaktion lauft wahrscheinlich nach einem Additions-Eliminierungs-Mechanismus ab. 3,4-Dihydro-6-rnethyl-l,Z-benzoxathiine 2,Z-Dioxide Derivatives with Enarninone Structures from Phenyl 6-Methyl-4-chromone-3-sulfonate Primary and secondary amines react with phenyl 6-methyl-4-chromone-3-sulfonate (5) to give 3,4-dihydro-6-methyl-1,2-benzoxathiine 2,2-dioxide derivatives 8 a -g with enaminone structures. Probably this ring transformation reaction takes place by an addition-elimination mechanism.

Wie bereits von uns gezeigt wurde, reagiert Chromon-3-sulfonylchlorid mit ethanolischer Methylamin-Losung zum 3,4-Dihydro-3-[(methylamino)methylen]-4-0x0-I ,2-benzoxathiin-2,2-dioxid2'.

In unsere weiteren Untersuchungen zum Verlauf dieser Ringtransformationsreaktion haben wir nun den 6-Methyl-4-chromon-3-sulfonsaure-phenylester (5) einbezogen, den wir aus der entsprechenden Sulfonsaure 2 uber deren Natriumsaiz 3 und das Sulfonylchlorid 4 herstellen konnten.

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