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Nenitzescu reaction of acetyl ketene aminals (N,N-acetals) was investigated. The interaction of 2-acetyl-l-amino-l-anilinoethene with benzoquinone gave 3-acetyl-2-amino-7a-hydroxy-l-phenyl-5,7a-dihydro-IH-indol-5-one, which was then transformed into 3-aeetyl-2-amino-6-chloro-5-hydroxy-l-phenylindole. The reaction of benzoquinone with 2-acetyi-lamino-l-benzoylaminoethene led to the corresponding hydroquinone-adduct which was oxidized to 4-acetylamino-5-(2,5-dihydroxyphenyl)-2-phenyloxazole.

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Ring closure reactions O 0130 Quinoneimines in the Nenitzescu Reaction. -Nenitzescu reaction involving quinoneimines provides access to new 5-aminoindole, 5-aminobenzofuran, and 9-aminochromenopyridine derivatives. -(LYUBCHANSKAYA, V. M.; PANISHEVA, E. K.; SAVINA, S. A.; ALEKSEEVA, L. M.; SHASHKOV, A. S.; GRANIK*, V. G.; Russ.

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Starting with the bromomethyl compound (I), the aminomethyl derivatives (III), (IV), and (VI) are prepared as shown in the reaction scheme.