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Thermal acyl shift in 2-acyloxy-2-penten-4-ones

✍ Scribed by Albrecht Mannschreck; Hans Dvorak

Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
238 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis

0-Acyl transfer has been detected for a number of 2-acyloxy-2-alken-4-ones, i.e. carboxylic esters of enols of 2,4-diones 2-4) . Formula 1 exemplifies this type of compounds, although acyl transfer was not known for this particular example. These observations 2-4) apparently do not permit safe conclusions about the intra-or intermolecular nature of these processes and whether they occur thermally, i.e. without extra-

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Substituted 3-hydroxyquinoline-2,4(1H,3H )-diones 3 were transformed into 3-acyloxy-1,3-dihydro-2H-indol-2-ones 4 and isomeric 4-acyl-1,4-dihydro-3,1-benzoxazin-2-ones 5. The influence of the substituents and the reaction conditions on the course of the reaction was studied. In the proposed mechanis