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

作者：Bianchi Lara^*; Giorgi Gianluca; Maccagno Massimo; Petrillo Giovanni; Scapolla Carlo; Tavani Cinzia

来源：Tetrahedron Letters, 2012, 53(7): 752-757.

DOI：10.1016/j.tetlet.2011.11.137

• Nitrobutadienes
• Nitrogen heterocycles
• Indoles
• Carbazoles
• Michael-type additions

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.

• 出版日期2012-2-15