Synthese und Deoxygenierung substituierter 1‐Azaadamantan‐4,6‐dione | Zendy

Risch Nikolaus | Zendy; Billerbeck Ulrich | Zendy; Krieger Evelyn | Zendy

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Synthese und Deoxygenierung substituierter 1‐Azaadamantan‐4,6‐dione

Author(s) -

Risch Nikolaus,

Billerbeck Ulrich,

Krieger Evelyn

Publication year - 1992

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19921250225

Subject(s) - chemistry , deoxygenation , hexamethylenetetramine , yield (engineering) , steric effects , medicinal chemistry , organic chemistry , bicyclic molecule , catalysis , materials science , metallurgy

Synthesis and Deoxygenation of Substituted 1‐Azaadamantane‐4,6‐diones 1‐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 NaBH 4 /MeOH and subsequent chlorination give the dichlorides 4 , which are dehalogenated with n Bu 3 SnH. Quaternary ammonium salts 6 are available in high yields.

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