An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes

The multifaceted behavior of nitrobutadienes deriving from the initial ring-opening of nitrothiophenes finds a further clear-cut example in their Michael-type acceptor reactivity towards indole. Thus, depending on the starting diene, either newly-functionalized indoles or carbazoles are produced, th...

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Bibliographic Details
Published in:Tetrahedron letters 2012-02, Vol.53 (7), p.752-757
Main Authors: Bianchi, Lara, Giorgi, Gianluca, Maccagno, Massimo, Petrillo, Giovanni, Scapolla, Carlo, Tavani, Cinzia
Format: Article
Language:English
Subjects:
Carbazoles
Indoles
Michael-type additions
Nitrobutadienes
Nitrogen heterocycles
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Summary:The multifaceted behavior of nitrobutadienes deriving from the initial ring-opening of nitrothiophenes finds a further clear-cut example in their Michael-type acceptor reactivity towards indole. Thus, depending on the starting diene, either newly-functionalized indoles or carbazoles are produced, the latter as the result of an appealing double (intermolecular+intramolecular) Michael-type addition to a nitrovinylic moiety. The outcome encompasses motifs for both mechanistic and synthetic interest in the field of heterocycles endowed with possible pharmacological activity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.11.137