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3,4-Dihydro-benz[1,3]oxazine Derivatives from 2-Acyl(or aroyl)-cyanatobenzenesDedicated to Prof. Dr. E. Schmitz on the occasion of his 65th birthday (1993)

Buttke, K. ; Ramm, M. ; Niclas, H.-J.

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 335 (1993), S. 544-548

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ISSN: 0941-1216

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/prac.19933350608

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