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. (C) 2011 Elsevier Ltd. All rights reserved.
Bianchi, L., Giorgi, G., Maccagno, M., Petrillo, G., Scapolla, C., Tavani, C. (2012). An Original Route to Newly-Functionalized Indoles and Carbazoles Starting from the Ring-Opening of Nitrothiophenes. TETRAHEDRON LETTERS, 53(7), 752-757 [10.1016/j.tetlet.2011.11.137].
An Original Route to Newly-Functionalized Indoles and Carbazoles Starting from the Ring-Opening of Nitrothiophenes
Giorgi G.;
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. (C) 2011 Elsevier Ltd. All rights reserved.
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https://hdl.handle.net/11365/33173
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