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Paper | Regular issue | Vol 36, No. 5, 1993, pp.995-1003
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6256
Structures of Saturated Azeto[1,2-a][3,1]- and Azeto[2,1-b][1,3]benzoxazines Prepared by Addition of Chloroacetyl Chlorides to Cyclohexane-condensed Dihydrooxazines

Géza Stájer, Angela E. Szabó, Ferenc Fülöp, Gábor Bernáth,* and Pál Sohár

*Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, H-6701 Szeged, Eötvö;s u.6., Hungary


Saturated cis and trans 3,1- and 1,3-benzoxazines (1-4) reacted with chloroacetyl chlorides to yield azeto[1,2-a][3,1]- and [2,1-b][1,3]benzoxazines (5, 6, 8, 9a,b). In one case, the addition took place with partial cistrans inversion of the starting compound. Adduct (7), containing two condensed 1,3-oxazine rings, was also isolated. The stereostructures of the new compounds were proved by 1H- and 13C-nmr spectroscopy, with NOE measurement data. The reaction mechanism is discussed.