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.
An Original Route to Newly-Functionalized Indoles and Carbazoles Starting from the Ring-Opening of Nitrothiophenes
BIANCHI, LARA;MACCAGNO, MASSIMO;PETRILLO, GIOVANNI;SCAPOLLA, CARLO;TAVANI, CINZIA
2012-01-01
Abstract
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.
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