Alan E. Moormann

Reductive Amination of Piperidines with Aldehydes Using Borane-Pyridine

Abstract Borane-pyridine complex (BAP) was found to be an excellent replacement for NaCNBH3 in the Borch reduction. Assorted aromatic, heterocyclic and aliphatic aldehydes were reacted with various substituted piperidines using standardized conditions.

The oxidation of aromatic amines in the presence of “electron-rich” aromatic systems

Abstract The oxidation of aromatic amines to the corresponding nitro substituents is performed under mild, nonacidic conditions in the presence of highly nucleophilic aromatic systems such as indoles and furans.

Selective heterocyclic amidine inhibitors of human inducible nitric oxide synthase

The potency and selectivity of a series of 5-hetero-2-iminohexahydroazepines were examined as inhibitors of the three human NOS isoforms. The effect of ring substitution of the 5-carbon for a heteroatom is presented. Potencies (IC(50)s) for these inhibitors are in the low micromolar range for hi-NOS with some examples exhibiting a 500x selectivity versus hec-NOS.

Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491

Abstract A racemic synthesis of azanoradamantane (±) -3 was accomplished via Yamamotos MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchens asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.

Enantioselective synthesis of dual 5-HT45-HT3 serotonergic azanoradamantane SC-52491

Abstract A racemic synthesis of azanoradamantane (±) -3 was accomplished via Yamamotos MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchens asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.

A Facile Synthesis of 2-Aminonicotinaldehyde

Abstract A synthesis of 2-aminonicotinaldehyde (1) which does not require chromatography and is easily scaled up has been developed. Bromination of 2-amino-3-picoline, protected as a phthalimide (4), produced the gem-dibromide (5), which was reacted with Nh4OH. The imine intermediate (7) was hydrolyzed with acid, producing (1) in a 56% conversion from 4.

Design and synthesis of agonists and antagonists of the serotonin 5-HT4 receptor subtype

Publisher Summary This chapter discusses the design and synthesis of agonists and antagonists of the serotonin 5-HT4 receptor subtype. Serotonin is unsurpassed among monoamine neurotransmitters in the number of receptor subtypes reported to-date. Fourteen subtypes of seven major serotonin receptor classes have been identified in the central nervous system, the peripheral nervous system, myeloid/immune cell types, and smooth musculature of mammals. For some time, it has been known that serotonin exerts profound effects in the enteric nervous system (ENS). It has been previously appreciated that 5-HT4 agonism requires a planar orientation of the amide bond and the aromatic ring system. This feature contributes to the potent agonist properties of the ortho-alkoxy benzamides i, wherein intramolecular hydrogen-bonding maintains such a planar conformation.