955378-71-9Relevant academic research and scientific papers
Gold-Catalyzed Aromatizations of 3-Ene-5-siloxy-1,6-diynes with Nitrosoarenes to Enable 1,4-N,O-Functionalizations: One-Pot Construction of 4-Hydroxy-3-aminobenzaldehyde Cores
Kale, Balaji S.,Liu, Rai-Shung
, p. 8434 - 8438 (2019/10/16)
This work describes gold-catalyzed aromatizations of 3-ene-5-siloxy-1,6-diynes with nitrosoarenes to form 4-hydroxy-3-aminobenzaldehyde derivatives, manifesting the use of nitrosoarenes as 1,4-N,O-functionalization sources. Various 3-ene-5-siloxy-1,6-diynes in benzoid and nonbenzoid types are applicable substrates. A series of 18O- and 2H-labeling experiments have been conducted to exclude gold-π-alkyne intermediates. We postulate a mechanism of dual gold catalysis involving initial formation of gold-π-alkynylgold species that activates a 1,5-hydrogen shift to form reactive 1,6-dipoles, thus furnishing intramolecular Michael-type reactions with nitrosonium electrophiles.
Gold-catalyzed Intermolecular Oxidations of 2-Ketonyl-1-ethynyl Benzenes with N-Hydoxyanilines to Yield 2-Aminoindenones via Gold Carbene Intermediates
Mokar, Bhanudas Dattatray,Huple, Deepak B.,Liu, Rai-Shung
, p. 11892 - 11896 (2016/11/16)
Gold-catalyzed oxidations of 2-ketonyl-1-ethynyl benzenes with N-hydroxyanilines yield 2-aminoindenone derivatives efficiently. Experimental data suggests that this process involves an α-oxo gold carbene intermediate, generated from the attack of N-hydroxyaniline on furylgold carbene intermediate, rather than the typical attack of oxidants on π-alkynes.
Synthesis of 2-azaanthracenes via a sequential Sonogashira coupling/alkynyl imine-allenyl imine isomerization/aza-Diels-Alder/elimination-aromatization reaction
Cao, Jian,Yang, Xiongfa,Hua, Xilin,Deng, Yuan,Lai, Guoqiao
, p. 478 - 481 (2011/03/23)
An interesting sequential Sonogashira coupling/alkynyl imine-allenyl imine isomerization/aza-Diels-Alder/elimination-aromatization reaction, providing a facile synthesis of substituted 2-azaanthracenes from 1,6-diynes and imidoyl chlorides, is reported. T
