Heteroadamantanes and their derivatives. 6. Synthesis and mass-spectrometric investigation of 5-mono- and 5,6-disubtituted 6-oxo-1,3-diazaadamantanes

Bispidine Coordination Chemistry

“…There was a controversy about the reaction pathway until it was shown that the initial product was 5,7-diphenyl-1,3-diazaadamantane-6-one (88). Following this observation the synthesis of various 1,3-diazaadamantane-6-ones with different substituents in the 5,7-position was reported (88)(89)(90), and these compounds found their way into the preparation of bispidine derivatives.…”

Synthesis of fragrant 1,3-diazaadamantan-6-ones

“…The same method was used to obtained two monosubstituted diazaadamantan one from the corresponding methyl ketones of the type RCH 2 COCH 3 (methyl ethyl and benzyl methyl ketones) in low yield: 5 methyl and 5 phenyl 1,3 diazaadaman tan 6 ones. 1 The low yields of monosubstituted diazaada mantanones as compared to the disubstituted ones are explained by the involvement of all five labile hydrogen atoms of methyl ketones in the condensation, as it was shown in our work. 10 Despite the low yields of monosubstituted diazaada mantanones, they are of theoretical and practical interest due to the fact that a number of methyl ketones are known as naturally occurring fragrances used in cosmetics, per fumery, and as food additives.…”

Copper–Bispidine Complexes: Synthesis and Complex Stability Study

“…Compounds 2a – c , 3b , and 3c were synthesized starting from urotropine and diethyl ketone by applying known sequences (Scheme ). ,,,,− Alkylation of compounds 1a – c was performed using different alkylating agents. Whereas the reactions with chloroacetic acid for the preparation of unbranched compounds 2a – c proceeded readily, the reactions with racemic 2-chloropropionic acid for the preparation of products 3b – c were rather slow, that is, the conversions at 3 h did not exceed 50%.…”