855749-08-5Relevant articles and documents
Gold(I)-catalyzed 1,2-acyloxy migration/[3+2] cycloaddition of 1,6-diynes with an ynamide propargyl ester moiety: Highly efficient synthesis of functionalized cyclopenta[b]indoles
Liu, Jun,Chen, Ming,Zhang, Liangwei,Liu, Yuanhong
, p. 1009 - 1013 (2015)
A gold-catalyzed cycloisomerization of 1,6-diynes containing an ynamide propargyl ester or carbonate moiety has been developed that provides an attractive route to a diverse-substituted 3-acyloxy-1,4-dihydrocyclopenta[b]indoles. Mechanistic studies indicate that the reaction likely proceeds through a competitive 1,2-OAc migration followed by [3+2] cycloaddition of the vinyl gold-carbenoid intermediate with the pendant triple bond. The synthetic utility of the obtained cyclopenta[b]indole products was demonstrated by their efficient transformations by deprotection or double-bond isomerization reactions.
Synthesis of carbazoles by dehydro Diels-Alder reactions of ynamides
Martínez-Esperón, M. Fernanda,Rodríguez, David,Castedo, Luis,Saá, Carlos
, p. 3674 - 3686 (2008/09/19)
A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder of ynamides is reported. N-(o-Ethynyl)aryl ynamides and N-(o-ethynyl) arylynamides were prepared in a few steps starting from o-iodoaniline. Thermal c
Coupling and cycloaddition of ynamides: Homo- and Negishi coupling of tosylynamides and intramolecular [4 + 2] cycloaddition of N-(o-ethynyl)phenyl ynamides and arylynamides
Martínez-Esperón, María Fernanda,Rodríguez, David,Castedo, Luis,Saá, Carlos
, p. 3843 - 3855 (2007/10/03)
N,N′-aryl- and N,N′-alkyl-buta-1,3-diyne-1,4-ditosylamides have been synthesized for the first time, in good to excellent yields, by copper-catalyzed dimerization of the corresponding N-aryl or N-alkyl tosylynamides. Negishi coupling of N-ethynylzinc tosy
Synthesis of carbazoles from ynamides by intramolecular dehydro Diels-Alder reactions
Martinez-Esperon, Maria Fernanda,Rodriguez, David,Castedo, Luis,Saa, Carlos
, p. 2213 - 2216 (2007/10/03)
(Chemical Equation Presented) A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder reactions of ynamides is reported. By using this approach, carbazoles and benzo[b]-, tetrahydrobenzo[b]-, naphtho[1,2-b]