118299-61-9Relevant academic research and scientific papers
Synthesis and Pharmacology of Site-Specific Cocaine Abuse Treatment Agents: The Role of the Phenyl Group in Highly Modified Methylphenidate analogs as Dopamine Uptake Inhibitors
Deutsch, Howard M.,Dunn, Travis,Ye, Xiaocong,Schweri, Margaret M.
, p. 213 - 222 (2007/10/03)
A series of modified methylphenidate derivatives was synthesized and tested for inhibitory potency in [3H]WIN 35,428 binding and [3H]dopamine uptake assays using rat striatal tissue. In these compounds the role of the phenyl ring was investigated by its r
Radical cyclization reactions of α-silyl amine α,β-unsaturated ketone and ester systems promoted by single electron transfer photosensitization
Jeon, Yoon T.,Lee, Chao-Pin,Mariano, Patrick S.
, p. 8847 - 8863 (2007/10/02)
The results of a broad investigation of the preparative and mechanistic aspects of single electron transfer (SET) promoted photocyclization reactions of α-silyl amino and amido α,β-unsaturated esters and ketones are presented. A number of unique and synthetically useful features of these processes, driven by α-silyl amine and amide cation radical desilylation and by intramolecular conjugate addition of intermediate α-amino and α-amido carbon-centered radicals to unsaturated esters and ketones, are described. Comparisons of the SET-sensitized and direct irradiation promoted reactions of these systems have shown how the former method is superior in inducing photocyclization reactions in cases where the α,β-unsaturated ketone or ester excited states are too reactive to be quenched by SET from the tethered amine donors and where diradicals produced as intermediates in the direct-irradiation reactions undergo fragmentation rather than cyclization. The current efforts have also demonstrated that problems associated with the ready oxidation of intermediate α-amino radicals can be avoided by the proper selection of photosensitizer or amine N substituents. Lastly, the synthetic versatility of this chemistry, exemplified by its application to the preparation of a number of N-heterocyclic substances by pathways involving either exo or endo radical cyclization, is presented.
