Synthesis of a library of tricyclic azepinoisoindolinones
| Autor: | Shuli Mao, Peter Wipf, Joshua G. Pierce, Bettina Miller, Kara M. George Rosenker |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2012 |
| Předmět: |
010402 general chemistry
Metathesis 01 natural sciences Full Research Paper lcsh:QD241-441 Aminolysis lcsh:Organic chemistry Organic chemistry chemical diversity lcsh:Science epoxide aminolysis chemistry.chemical_classification 010405 organic chemistry Alkene isoindolinones N-acyliminium ion Organic Chemistry Alkene epoxidation Combinatorial chemistry 0104 chemical sciences Chemistry chemistry Chemical diversity lcsh:Q metathesis Isomerization PubChem Tricyclic hydrozirconation |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 8, Iss 1, Pp 1091-1097 (2012) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | Hydrozirconation of 1-hexyne, the addition to in situ prepared N-acyliminium species, and ring-closing metathesis (RCM) were key steps in the preparation of a tricyclic isoindolinone scaffold. An unusual alkene isomerization process during the RCM was identified and studied in some detail. Chemical diversification for library synthesis was achieved by a subsequent alkene epoxidation and zinc-mediated aminolysis reaction. The resulting library products provided selective hits among a large number of high-throughput screens reported in PubChem, thus illustrating the utility of the novel scaffold. |
| Databáze: | OpenAIRE |
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