Synthesis of Novel Polycyclic Carbamate Derivatives of 2-Hydroxy-2,2′-biindane-1,1′,3,3′-tetrone

Abstract

Methyl 1,3,11′-trioxo-1,3,10a′,11′-tetrahydro-4β′H-spiro[inden-2,10′-indeno[1,2-b]chromene]-7′(8′)-ylcarbamates and methyl(ethyl) 4-(1,1′,3,3′-tetraoxo-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biinden-2-yl)-phenylcarbamates were synthesized by condensation of 2-hydroxy-2,2′-biindane-1,1′,3,3′-tetrone with methyl N-(3(4)-hydroxyphenyl)carbamates and methyl(ethyl) N-phenylcarbamates. Condensation of methyl N-(2-hydroxyphenyl)-carbamate with the tetrone gave methyl 2-hydroxy-5-(1,1′,3,3′-tetraoxo-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biinden-2-yl)phenylcarbamate. Methyl 4-(3′-amino-1,1′,3-trioxo-2,3-dihydro-1H,1′H-2,2′-biinden-2-yl)-phenylcarbamate was obtained by boiling methyl 4-(1,1′,3,3′-tetraoxo-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biinden-2-yl)-phenylcarbamate with urea in glacial acetic acid. Condensation of methyl 4-(1,1′,3,3′-tetraoxo-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biinden-2-yl)-phenylcarbamate with hydrazine hydrate at room temperature gave methyl N-{4-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)(4-oxo-3,4-dihydro-1-phthalazinyl)methyl]phenyl}-carbamate.