474267-03-3Relevant academic research and scientific papers
Copper-catalyzed synthesis of indole-fused benzodiazepines
Biswas, Subhasish,Batra, Sanjay
supporting information; experimental part, p. 2861 - 2867 (2011/12/01)
The copper-catalyzed synthesis of indole-fused benzodiazepine via a cascade reaction between 3-halo-1H-indole-2-carbaldehydes and substituted 1,2-phenylenediamines is reported. Reactions with N-Boc-protected indole-aldehydes are found to be more efficient
Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes
Zhang, Haiming,Larock, Richard C.
, p. 7048 - 7056 (2007/10/03)
A variety of 3-substituted β- and γ-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes with PdCl2(PPh3)2/CuI as the catalyst readily affords the corresponding alkynylindole carboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines and cyclized to β- and γ-carbolines by either copper-catalyzed or thermal processes.
Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of alkynes
Zhang, Haiming,Larock, Richard C.
, p. 9318 - 9330 (2007/10/03)
A variety of substituted β- and γ-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting β-carboline alkaloids, ZK93423 and abecarnil (ZK112119).
