Synthesis and structural and conformational study of some amines derived from the norgranatane system

Fernández, M. J.; Huertas, R.; Galvez, Enrique J.

doi:10.1016/0022-2860(91)80139-u

Cited by 19 publications

(4 citation statements)

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“…A coupling constant of 11.0 Hz between the 2- exo and the bridgehead 1-proton was observed that is indicative of an eclipsed arrangement. Thus, the obtained 1 H NMR data are in agreement with a 3- exo proton and a boat−chair conformation of the granatane. , …”

Section: Resultssupporting

confidence: 83%

“…Thus, the obtained 1 H NMR data are in agreement with a 3-exo proton and a boat-chair conformation of the granatane. 13,20 This particular structural aspect of granisetron derivatives 2-7 was further confirmed by the crystal structures of 4b and 5a (Figures 1 and 2). In both structures the indazole ring is coplanar with the amide bond and there appears to be flexibility around the bond between the amide nitrogen and the granatane.…”

Section: Resultssupporting

confidence: 55%

“…Thus, the obtained 1 H NMR data are in agreement with a 3- exo proton and a boat−chair conformation of the granatane. 13 , 20 …”

Section: Resultsmentioning

confidence: 99%

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Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

et al. 2010

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This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT3A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one such position and specifically bound to 5-HT3A receptors in mammalian cells.

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Section: Resultssupporting

confidence: 83%

Section: Resultssupporting

confidence: 55%

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Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

et al. 2010

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“…Both the formation of sole 3-endoisomers 40b [42] and of mixtures 40b/41b (endo/exo ≈ 2:1) [39] were reported for the reductive amination of a pseudopelletierine 36b with sodium cyanoborohydride and various amines. Catalytic hydrogenation of in situ generated imine 38a (R 1 = H) and oxime 37b serves for commercial syntheses of endo-3-tropylamine 34a and endo-3-granatylamine 34b on an industrial scale, respectively [43].…”

Section: ____________________________________________________________mentioning

confidence: 98%

Complementary Ways to Diastereomers of Bridged Aminopiperidine Derivatives - A Stereochemical Challenge

Vilsmaier¹

2000

J. prakt. Chem.

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Abstract. Routes to diastereomers of constrained 4-aminopiperidines -a common pharmaceutically used diaminic building block -are realized mainly on the basis of CN-double bond species or their radicalic or anionic analogues. Kinetically controlled reactions on the one hand and thermodynamic control of reactions, reversible introduction of a repulsive group, direction of a reactant by intramolecular complexation, or involvement of radicalic or anionic intermediates with strong isomerization tendency on the other hand are the tools for a complementary accessibility of both diastereomers.

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Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

2002

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Reductive amination is an important tool for synthetic organic chemists in the construction of carbon‐nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron‐withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful. This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron‐containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen‐containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron‐containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.

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Synthesis and structural and conformational study of some amines derived from the norgranatane system

Cited by 19 publications

References 10 publications

Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

Complementary Ways to Diastereomers of Bridged Aminopiperidine Derivatives - A Stereochemical Challenge

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

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Synthesis and structural and conformational study of some amines derived from the norgranatane system

Cited by 19 publications

References 10 publications

Toward Biophysical Probes for the 5-HT3 Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

Toward Biophysical Probes for the 5-HT3 Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

Complementary Ways to Diastereomers of Bridged Aminopiperidine Derivatives - A Stereochemical Challenge

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

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Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives