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Synthese und Deoxygenierung substituierter 1-Azaadamantan-4,6-dione (1992)

Risch, Nikolaus ; Billerbeck, Ulrich ; Krieger, Evelyn

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 459-465

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ISSN: 0009-2940

Keywords: 1-Aza-4,6-adamantanedione derivatives synthesis ; Radical deoxygenation, nBu3SnH ; Ammonium salts ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Synthesis and Deoxygenation of Substituted 1-Azaadamantane-4,6-diones1-Azaadamantanes 5 and a variety of derivatives are accessible by a triple Mannich reaction of 1,3-cyclohexanediones 1 with hexamethylenetetramine to yield the 1-azaadamantane-4,6-diones 2. Deoxygenation of the sterically hindered and non-enolizable β-dioxo group in 2 succeeds by radical processes. Treatment with NaBH4/MeOH and subsequent chlorination give the dichlorides 4, which are dehalogenated with nBu3SnH. Quaternary ammonium salts 6 are available in high yields.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19921250225

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