497236-36-9Relevant academic research and scientific papers
Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines
Wang, Hong-Fa,Wang, Shi-Yue,Qin, Tian-Zhu,Zi, Weiwei
, p. 17911 - 17914 (2018/11/23)
This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.
Gold(I)-Catalyzed Formal Intramolecular Dehydro-Diels-Alder Reaction of Ynamide-ynes: Synthesis of Functionalized Benzo[ b]carbazoles
Xu, Wei,Wang, Gaonan,Xie, Xin,Liu, Yuanhong
supporting information, p. 3273 - 3277 (2018/06/11)
A gold-catalyzed cycloisomerization of ynamide-ynes via a formal dehydro-Diels-Alder reaction has been developed, providing an attractive route to diversely substituted benzo[b]carbazoles. The reaction likely proceeds via regioselective attack of the pendant alkyne moiety to a keteniminium ion intermediate followed by benzannulation. The method offers several advantages such as high efficiency, mild reaction conditions, and wide functional group tolerance and serves as a highly useful complement to the thermal DDA reactions of ynamide-ynes.
Synthesis of β- And γ-carbolines via ruthenium and rhodium catalysed [2+2+2] cycloadditions of yne-ynamides with methylcyanoformate
Nissen, Felix,Richard, Vincent,Alayrac, Carole,Witulski, Bernhard
, p. 6656 - 6658 (2011/06/27)
A flexible approach towards substituted β- and γ-carbolines based on transition metal catalysed [2+2+2] cycloaddition reactions between functionalised yne-ynamides and methylcyanoformate is described. The versatility of this new reaction sequence is demon
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
A highly efficient and flexible synthesis of substituted carbazoles by rhodium-catalyzed inter- and intramolecular alkyne cyclotrimerizations
Witulski, Bernhard,Alayrac, Carole
, p. 3281 - 3284 (2007/10/03)
An A→ABC or A→ABCD ring-formation strategy proves extremely efficient for generating substituted carbazoles ([Eq. (1)]; Ts = tosyl). Inter- and intramolecular alkyne cyclotrimerizations mediated by Wilkinson's catalyst provide substituted carbazoles of re
