An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes
Lara Bianchi
1
,
Gianluca Giorgi
2
,
Massimo Maccagno
1
,
G. Petrillo
1
,
Carlo Scapolla
1
,
Cinzia Tavani
1
Publication type: Journal Article
Publication date: 2012-02-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
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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GOST
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Bianchi L. et al. An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes // Tetrahedron Letters. 2012. Vol. 53. No. 7. pp. 752-757.
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Bianchi L., Giorgi G., Maccagno M., Petrillo G., Scapolla C., Tavani C. An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes // Tetrahedron Letters. 2012. Vol. 53. No. 7. pp. 752-757.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2011.11.137
UR - https://doi.org/10.1016/j.tetlet.2011.11.137
TI - An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes
T2 - Tetrahedron Letters
AU - Bianchi, Lara
AU - Giorgi, Gianluca
AU - Maccagno, Massimo
AU - Petrillo, G.
AU - Scapolla, Carlo
AU - Tavani, Cinzia
PY - 2012
DA - 2012/02/01
PB - Elsevier
SP - 752-757
IS - 7
VL - 53
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
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@article{2012_Bianchi,
author = {Lara Bianchi and Gianluca Giorgi and Massimo Maccagno and G. Petrillo and Carlo Scapolla and Cinzia Tavani},
title = {An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes},
journal = {Tetrahedron Letters},
year = {2012},
volume = {53},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.tetlet.2011.11.137},
number = {7},
pages = {752--757},
doi = {10.1016/j.tetlet.2011.11.137}
}
Cite this
MLA
Copy
Bianchi, Lara, et al. “An original route to newly-functionalized indoles and carbazoles starting from the ring-opening of nitrothiophenes.” Tetrahedron Letters, vol. 53, no. 7, Feb. 2012, pp. 752-757. https://doi.org/10.1016/j.tetlet.2011.11.137.