Synthesis of Heterocyclic Analogues of Epibatidine via 7-Azabicyclo[2.2.1]hept-2-yl Radical Intermediates. 1. Intermolecular Reactions
| Autor: | Elena Gomez‐Sanchez, José Marco-Contelles, Elena Soriano |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Reaction mechanism Cyanides Acrylonitrile Free Radicals Nitrile Intramolecular reaction Bicyclic molecule Pyridines Stereochemistry Organic Chemistry Stereoisomerism Receptors Nicotinic Bridged Bicyclo Compounds Heterocyclic Medicinal chemistry Chemical synthesis Heptanes chemistry.chemical_compound Models Chemical chemistry Reactivity (chemistry) Nicotinic Agonists Azabicyclo Compounds Alkyl |
| Zdroj: | The Journal of Organic Chemistry. 73:6784-6792 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The synthesis and reactivity of the 7-azabicyclo[2.2.1]hept-2-yl radical has been extensively investigated in inter- and intramolecular reaction processes for the first time. In this work we will present the preparation of the radical and its successful intermolecular reaction with radical acceptors such as tert-butylisocyanide and acrylonitrile. Computational analyses have been carried out to show and explain the mechanisms and stereochemical outcome of these transformations. Overall and from the chemical point of view, a new and convenient synthetic approach has been developed for the synthesis of exo-2-(cyano)alkyl substituted 7-azabicyclo[2.2.1]heptane derivatives, a series of compounds of wide interest for the synthesis of heterocyclic analogues of epibatidine. As a result, we describe here the synthesis of the tetrazoloepibatidines (8 and 15) and the oxadiazoloepibatidine (10). |
| Databáze: | OpenAIRE |
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