Synthesis of 5,7-nonamethylene-1,3-diazaadamantan-6-one

Razenko, I. O.; Serova, T. M.; Кузнецов, А. И.

doi:10.1007/s11172-016-1606-6

Cited by 2 publications

(2 citation statements)

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“…It is known that bispidines can be obtained not only from substituted piperidones, which are not always commercially available or have the above restrictions on substituents at nitrogen atoms but also from urotropine and ketones with an active methylene moiety, 27,28 bispidine, the methylene bridge between the nitrogen atoms is removed by reaction with anhydrides or acid halides. 29,30 The methylene bridge removal reaction presumably proceeds stepwise with the formation of an active methylene moiety that resembles a Mannich salt (Scheme 2).…”

Section: ■ Introductionmentioning

confidence: 99%

“…It is known that bispidines can be obtained not only from substituted piperidones, which are not always commercially available or have the above restrictions on substituents at nitrogen atoms but also from urotropine and ketones with an active methylene moiety, , except for acetone. To obtain bispidine, the methylene bridge between the nitrogen atoms is removed by reaction with anhydrides or acid halides. , …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of N,N′-Unsymmetrical 9-Amino-5,7-dimethyl-bispidines

et al. 2023

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A new approach to the preparation of N,N′-unsymmetrically substituted 9-aminobispidines through aminal bridge removal reaction has been developed, the principal feature of which is the ability to selectively functionalize all three nitrogen atoms. The intermediates of 1,3diazaadamantane's aminal bridge removal reaction are characterized, and the mechanism of this reaction is proposed based on the analysis of their structures. Representatives of the previously unknown saturated heterocyclic 1,5,9-triazatricyclo[5.3.1.0 3,8 ]undecane system were obtained and structurally characterized. Thus, it was possible for the first time to obtain 3,7,9trisubstituted bispidines containing acetyl, Boc, and benzyl groups at nitrogen atoms, which can be independently removed (orthogonal protective groups).

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Section: ■ Introductionmentioning

confidence: 99%

“…It is known that bispidines can be obtained not only from substituted piperidones, which are not always commercially available or have the above restrictions on substituents at nitrogen atoms but also from urotropine and ketones with an active methylene moiety, , except for acetone. To obtain bispidine, the methylene bridge between the nitrogen atoms is removed by reaction with anhydrides or acid halides. , …”

Section: Introductionmentioning

confidence: 99%