Divergent base-induced reactivity of cycloalkenyl-1-diazenes

The different base-promoted regioselectivities of the ring closure processes in the reactions between cycloalkenyl-1-diazenes and β-ketoesters are investigated. Under the appropriate conditions it is possible to turn the synthesis towards cycloalkenyliden-pyrroles or functionalized 3-hydroxy-hydroci...

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Bibliographic Details
Published in:Tetrahedron 2010-08, Vol.66 (34), p.6832-6841
Main Authors: Attanasi, Orazio A., Berretta, Stefano, De Crescentini, Lucia, Favi, Gianfranco, Filippone, Paolino, Giorgi, Gianluca, Mantellini, Fabio
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:The different base-promoted regioselectivities of the ring closure processes in the reactions between cycloalkenyl-1-diazenes and β-ketoesters are investigated. Under the appropriate conditions it is possible to turn the synthesis towards cycloalkenyliden-pyrroles or functionalized 3-hydroxy-hydrocinnolines. The aromatization procedure of the heteroring counterpart of the 3-hydroxy-hydrocinnolines is also reported. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.06.061