- Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds ('1,2,3-Triones'). Part 3. Polar and Redox Reactions of 1,2,3-Triones with Enamines of Different Types - News on Oxonol Dyes, Radicals, and Biradicals
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The central C=O groups of cyclic 1,2,3-triones possess outstanding electrophilic (electron-pair-accepting) as well as oxidizing (one-electron-accepting) properties. Thus, 1,2,3-triones are chemically related to 1,2- and 1,4-benzoquinones. Whereas polar reactions with carbanion-like (electron rich) species give rise to nucleophilic addition reactions to C=O groups under exclusive C,C-bond formation, SET (single-electron transfer) or redox reactions effect a partial 'carbonyl Umpolung' via ketyl intermediates (C,C- and/or C,O-bond formation). Here, we report on numerous reactions between electron-rich, more- or less-polar enamines with 5,5-dimethylcyclohexane-1,2,3-trione (9a) and 1H-indene-1,2,3-trione (9b). Various new derivatives of basic oxonol dyes were formed, including the first oxonol dye incorporating a 1,3-dioxocyclohexyl moiety. A novel stable radical, 50/50′, was obtained from 9b and lla via addition, hydrolysis, and treatment with conc. H2SO4. Radical 50/50′ represents a vinylogous 'monodehydroreductone' and is, thus, related to monodehydroascorbic acid (143), to Russell's radical cation (144), to indigo (141/141′), and to quinhydrone.
- Schank, Kurt,Lieder, Robert,Lick, Carlo,Glock, Rebecca
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p. 869 - 924
(2007/10/03)
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- An efficient route to biologically active 5H-indeno[1,2-c]pyridazin-5-ones
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A convenient and practical synthesis of 3 and 3,4 substituted 5H-indeno[1,2-c]pyridazin-5-ones has been developed starting from easily available ninhydrin and methyl or α-methylene ketones.
- Carotti,Carta,Campagna,Altomare,Casini
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p. 137 - 141
(2007/10/02)
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- "ONE-STEP" SYNTHESIS OF AN INDENO-INDOLILZINE NUCLEUS
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The reaction of 2-hydroxy-2-phenacyl-1,3-indanedione with tosyl chloride in pyridine directly afforded in high yield the 11-benzoyl-10H-indenoindolizine-10-one the structure of which has been determined by single crystal X-ray diffraction.A possibl
- Carotti, Angelo,Casini, Giovanni,Gavuzzo, Enrico,Mazza, Fernando
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p. 1659 - 1669
(2007/10/02)
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