Five-membered 2,3-dioxo heterocycles: LXII. Reaction of 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with N,N′-dihydroxycyclohexane-1,2-diamine. Unusual rearrangement in the spiro[quinoxaline-2,2′-pyrrole] system

3-Aroyl-1 H -pyrrolo[2,1- c ][1,4]benzoxazine-1,2,4-triones reacted with N,N′ -dihydroxycyclohexane-1,2-diamine to give 3-aroyl-1′,4,4′-trihydroxy-1-(2-hydroxyphenyl)-4a′,5′,6′,7′,8′,8a′-hexahydro-1′ H -spiro[pyrrole-2,2′-quinoxaline]-3′,5(1 H ,4′ H )-diones which underwent rearrangement into 1′-aro...

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Veröffentlicht in:Russian journal of organic chemistry 2008-08, Vol.44 (8), p.1189-1193
Hauptverfasser: Mashevskaya, I. V., Aliev, Z. G., Mazhukin, D. G., Popov, S. A., Tikhonov, A. Ya, Maslivets, A. N.
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Sprache:eng
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Zusammenfassung:3-Aroyl-1 H -pyrrolo[2,1- c ][1,4]benzoxazine-1,2,4-triones reacted with N,N′ -dihydroxycyclohexane-1,2-diamine to give 3-aroyl-1′,4,4′-trihydroxy-1-(2-hydroxyphenyl)-4a′,5′,6′,7′,8′,8a′-hexahydro-1′ H -spiro[pyrrole-2,2′-quinoxaline]-3′,5(1 H ,4′ H )-diones which underwent rearrangement into 1′-aroyloxy-4,4′-dihydroxy-1-(2-hydroxyphenyl)-4a′,5′,6′,7′,8′,8a′-hexahydro-1′ H -spiro[pyrrolidine-2,2′-quinoxaline]3′,4,5(4′ H )-triones via [1,4]-migration of the aroyl group. The product structure was proved by X-ray analysis.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428008080149