1373883-97-6Relevant articles and documents
3-alkenylation or 3-alkylation of indole with propargylic alcohols: Construction of 3,4-dihydrocyclopenta[ b ]indole and 1,4-dihydrocyclopenta[ b ]indole in the presence of different catalysts
Zhang, Li,Zhu, Yuanxun,Yin, Guangwei,Lu, Ping,Wang, Yanguang
, p. 9510 - 9520 (2013/01/15)
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.