3.7- Diazabicyclo nonane derivatives

A number of complexes were obtained with the 3,7-diazabicyclo[3.3.1]-nonane derivatives. Single-crystal X-ray diffraction data were reported for... 

The final step to 46 is cyclocondensation of 3,7-diazabicyclo[3.3.1]nonane (51), bispidine70, with formaldehyde. There are two different approaches to 51 (i) a pyridine is converted to a piperidine and (ii) the double Mannich or Robinson-Schopf condensation of ketone 52 with formaldehyde and primary amines affords 1,5-disubstituted 3,7-dazabicyclo[3.3.1]nonan-9-one (53), bispidone, from which 5,7-disubstituted l,3-diazaadamantan-6-one (61) is derived. Route (i) is adopted by Galinovsky and Langer,71 Stetter and... 

Isomeric l,3-diaza-6-thiaadamantane 6,6-dioxide (232) is prepared by cyclocondensation of 3-benzenesulfonyl-9-thia-3,7-diazabicyclo[3.3.1]nonane-9,9-dioxide (233) with formaldehyde, where 233 is derived from /V-benzene-sulfonyl-2,6-dimethylthiomorpholine (234).2 54... 

A similar vinylogous Mannich reaction has been used by Martin in the total syntheses of the heteroyohimboid alkaloids (—)-ajmalicine and (—)-tetrahydroalstonine <1995JOC3236>. An attempted synthesis of an opioid analgesic 2,4-dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one-l,5-dicarboxylate (piperidone) by a double Mannich reaction of oxoglutarate, 2 equiv of phenylacetaldehyde, and methylamine did not give the expected product but instead gave rise to an unexpected [l,6]naphthyridine derivative (Scheme 57) <1998PHA442>. 

An enzymatic method for resolution of the racemic cis-2,8-diazabicyclo[4.3.0[-nonane has also been described, in which reaction of the S,S-enantiomer with ethyl acetate in the presence of lipase produces the S,S-diacetyl derivative under the reaction conditions and the R, K-eriari liorner is only reacted to form the monoacetyl derivative. The components can be readily separated from the resulting reaction mixture, and then deacetylated [141]. 

N-Alkyl and N-Acyl Derivatives of 3,7-Diazabicyclo-[3.3.1] Nonanes and Selected Salts Thereof as Multiclass Antirrhythmic Agents... 

Selenium 3,7-diazabicyclo-[3.3.1]nonan-9-one derivatives have also been prepared by the author (2) as illustrated in Eq. 2 ... 

Gonzales Trigo. G.. Galvez Ruano, E., and Mcnendez Aguirre. C.. Spiro heterocyclic derivatives. XV. Some N-methyl-N -alkyl (or aralkyl) -3.7-diazabicyelo 0. 3.3.1 nonan-9-ones and. some, spiro-5 -hydanioin derivatives of 3,7-diazabicyclo(3.3.l Inonanes. An. Quim.. 75, 894, 1979 Chem Ahstr., 93. 26411, 1980. 

X-ray studies of a series of 1,5-diphenyl /V,/V -disubstituted derivatives of 3,7-diazabicyclo[3.3.1]nonan-9-one have shown that their conformation depends on whether the lone-pair electron density is delocalized away from the... 

The bispidine backbone (bispidine= 3,7-diazabicyclo[3.3.1]nonane) I is a simplified derivative of the natural product sparteine, 2 (see Chart 1 shown is the structure of a-isosparteine). Sparteine, a polycyclic alkaloid, occurs in a wide range of plants and has a variety of medical and chemical applications. It has been investigated extensively, for example, as a cardiac antiarrhyfhmia (1, 2), an ion channel blocker (3,4), and an uterotonic dmg (5). It was also used as a chiral base... 

The work on this ring system has been confined to perhydro derivatives related to constituents of certain ergot alkaloids. The saturated heterocycle has been described as l-oxa-6,9-diazabicyclo[4.3.0]nonane (11). Attention has been directed towards the study of the tautomerism of these... 

FIGURE 11.71 Bispidine derivatives library. (From Ivachtchehko, A.V. et al., A parallel solution phase synthesis of substituted 3,7-diazabicyclo[3.3.1]nonanes, J. Comb. Chem., 6, 828, 2004.)... 

Use of the Beckmann reaction in the quinuclidon-3 series and interaction of the bicyclic ketone (VI) with hydrazoic acid under Schmidt conditions gave rise to a new type of 1-azabicyclic system derivatives of 1,4-diazabicyclo-(3,2,2)-nonane (XLIV) [117-119]. 

Bartel S, Jaetsch T, Himmler T (1997) 8-Cyano-l-cyclopropyl-7-(2,8-diazabicyclo[4.3.0] nonan-8-yl)-6-fluoro-l,4-dihydro-4-oxo-3-qiunoline-carboxylic add derivatives. WO Patent 31001, 28 Aug 1997... 

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