Synthesis, Stereochemical, and Conformational Studies of Selected 3,7-Diheterabicyclo[3.3.1]nonan-9-ols: X-Ray Diffraction Analyses of 7-Benzyl-9-phenyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ol and 7-Benzyl-9-(4-<b><i>N,N′</i></b>-dimethylaminophenyl)-3-thia-7-azabicyclo[3.3.1]nonan-9-ol, a Rare Stable Chair–Boat Form With Trigonal Nitrogen

Based upon the analysis of 1 H NMR data, along with molecular modeling, it was shown that the reduction of 3,7-dihetera(N,N-; N,O-; N,S-)bicyclo[3.3.1]nonan-9-ones by LiAlH 4 led to a mixture of two stereoisomeric secondary alcohols with different orientations of the hydroxyl groups in one of the ring systems. Diaza derivatives in deuterochloroform exist in predominant chair-boat conformations. However, the replacement of nitrogen in one of the heterocycles by oxygen or sulfur led to stereoisomers one of which existed in chair-boat conformation and another in a chair-chair conformation. In all cases the boat conformation is stabilized by formation of an intramolecular hydrogen bond (IMHB) between a lone electron pair of the nitrogen atom and a proton on the pseudo axial hydroxyl group of the other ring.

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Cited by 3 publications

References 37 publications

Thiopyrans and Their Benzo Derivatives

Thiopyrans and Their Benzo Derivatives

Design, Synthesis, and Characterization of SO₂-Containing Azabicyclo[3.n.1]alkanes: Promising Building Blocks for Drug Discovery

Unusual Conformational Behavior of 3,7-Dihetera(N,N-;N,O-;N,S-) Bicyclo[3.3.1]Nonan-9-Ols Via Nmr Analysis

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Cited by 3 publications

References 37 publications

Thiopyrans and Their Benzo Derivatives

Thiopyrans and Their Benzo Derivatives

Design, Synthesis, and Characterization of SO2-Containing Azabicyclo[3.n.1]alkanes: Promising Building Blocks for Drug Discovery

Unusual Conformational Behavior of 3,7-Dihetera(N,N-;N,O-;N,S-) Bicyclo[3.3.1]Nonan-9-Ols Via Nmr Analysis

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Design, Synthesis, and Characterization of SO₂-Containing Azabicyclo[3.n.1]alkanes: Promising Building Blocks for Drug Discovery