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3-Alkenylation or 3-Alkylation of Indole with Propargylic Alcohols: Construction of 3,4-Dihydrocyclopenta[b]indole and 1,4-Dihydrocyclopenta[6]indoIe in the Presence of Different Catalysts.
- Source :
-
Journal of Organic Chemistry . 11/2/2012, Vol. 77 Issue 21, p9510-9520. 12p. - Publication Year :
- 2012
-
Abstract
- 3-Alkenylation or 3-alkylation of indole with propargylic alcohols could be efficiently controlled by the catalyst. In the presence of triflic acid, 3-alkenylation of indole occurred and a 3,4-dihydrocyclopenta[b] indole skeleton was effectively constructed in moderate to excellent yields via a cascade process. In the presence of Cu(OTf)2, 3-alkylation of indole resulted in the formation of 3-propargylic indole, which could be further converted into 2-iodo-1,4-dihydrocyclopenta[b]indoles in the presence of N-iodosuccinimide and boron trifluoride etherate. Possible mechanisms related to the 3-alkenylation or 3-alkylation of indole and their extension to the formation of 3,4-dihydrocyclopenta[b]indoles or 1,4-dihydrocyclopenta[b]indoles are postulated and discussed. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKENYLATION
*ALKYLATION
*INDOLE
*ALCOHOLS (Chemical class)
*BORON trifluoride
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 77
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 84110317
- Full Text :
- https://doi.org/10.1021/jo300339a