Journal fur Praktische Chemie - Chemiker-Zeitung p. 544 - 548 (1993)
Update date:2022-07-31
Topics:
Buttke, K.
Ramm, M.
Niclas, H.-J.
3,4-Dihydro-2H-benz<1,3>oxazin-2-ones 3 are obtained from 2-acyl(or aroyl)-cyanatobenzenes 2 and anisole.The reaction proceeds under Friedel-Crafts conditions via DIMROTH rearrangement.Compounds 2, dissolved in diethyl ether, react with 1 in the presence of finely powdered KOH at ambient temperature leading to 8.The structure of 8b is confirmed by X-ray structure analysis. (Z)-4-Ethylidene-3,4-dihydro-2H-benz<1,3>oxazin-2-one 9 is formed upon treatment of 2-cyanatopropiophenone 2b with diluted hydrochloric acid.The ethylene derivative 5 is obtained from 4 upon reaction with cyanogen bromide/triethyl amine.
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