The subject of this thesis is the development of a potentially simple, general and economical synthetic protocol for the potent antimalarial alkaloid febrifugine (1) and its analogues. In Chapter 1, the interesting history of 1, which includes a description of several reported total syntheses of 1, is discussed. Natural products derived from 1, as well as promising synthetic derivatives that di...

An efficient green chemistry approach to the synthesis of N-substituted piperidones and piperidines was developed and applied to the synthesis of 1-(2-pyridinylmethyl)-piperidin-4-one, 1, a key starting material for the synthesis of LY317615, an antiangiogenic agent currently under development at Eli Lilly and Company (Chart 1).(1) The general utility of this methodology, which presents signifi...

Discriminative stimulus effects of the serotonin (5-HT) receptor agonist 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) have been studied in rats and, more recently, in rhesus monkeys. This study examined DOM, 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7), and dipropyltryptamine hydrochloride (DPT) alone and in combination with three antagonists, MDL100907 [(+/-)2,3-dimethoxyphen...

In the title compound, C(18)H(22)BrN(3)OS, the piperidine ring adopts a chair conformation. The mean plane of the thia-zole ring forms dihedral angles of 23.97 (10) and 75.82 (10)° with the mean planes of its adjacent benzene and piperidine rings, respectively. An intra-molecular N-H⋯N hydrogen bond generates an S(7) ring motif in the mol-ecule. In the crystal, no significant inter-moelcular hy...

In the title compound, C(22)H(23)FN(2)OS, the piperidine ring shows chair confirmation and the two benzene rings make a dihedral angle of 17.0 (6)°. The thia-zole fragment is essentially planar with an r.m.s. deviation of 0.004 (2) Å and a maximum deviation of 0.006 (2) Å.. In the crystal, inter-molecular C-H⋯π inter-actions lead to the formation of a layer structure.

In the title compound, C(23)H(25)BrN(4)O(3)S(2), the benzene rings bridged by the sulfonamide group are tilted relative to each other by 69.7 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 70.4 (1)°. The mol-ecular conformation is stabilized by a weak intra-molecular π-π stacking inter-action between the pyrimidine and the 4-methyl benzene rings [centroid...