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Synthese und Reaktivität von 2- und 3-hydroxylierten Dihydro-1,4-Benzoxazinen

 

作者: HerbertBartsch,   WolfgangKropp,   MatthiasPailer,  

 

期刊: Monatshefte für Chemie / Chemical Monthly  (Springer Available online 2004)
卷期: Volume 110, issue 2  

页码: 267-278

 

ISSN:0026-9247

 

年代: 2004

 

DOI:10.1007/BF00911914

 

出版商: Springer_Vienna-Vienna

 

数据来源: Springer

 

摘要:

2can be pyrrolized to yield3 a, which in turn may be hydrolyzed with HCl to3 b. Acetylation of3 afollowed by a reaction with trifluoroacetic acid (TFA) gives3 e. Elimination of ethanol from3 aor of water from3 eis not possible. Treatment of1 awith pyridine/acetic anhydride andTFAor with acetic acid/acetic anhydride affords4 aand4 b, resp. Reaction of4 bin benzene/p-toluenesulfonic acid for 2 hours yields both ethers5Iand5II, whereas after 6 hours 4-acetyl-4H-1,4-benzoxazine (6) is obtained. The structures of all products are established by chemical and spectroscopic methods.

 

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