62002-15-7Relevant academic research and scientific papers
Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines
Magné, Valentin,Marinetti, Angela,Gandon, Vincent,Voituriez, Arnaud,Guinchard, Xavier
, p. 4036 - 4042 (2017)
N-Propargyl tryptamines bearing N-substituents such as propargyl, allyl, alkyl or benzyl groups undergo regioselective gold-catalyzed cyclizations to the corresponding spiroindolenines, while it was previously shown that N-sulfonyl-N-propargyl tryptamines lead to achiral azepino[4,5-b]indoles. An asymmetric approach to these spiroindolenines is disclosed using chiral gold complexes, leading to enantiomeric ratios up to 84/16. The spiroindolenines could be late-stage functionalized using Huisgen cyclizations, palladium-catalyzed cross couplings or reductions. Computational studies show that the reaction evolves via different mechanistic pathways depending on the nature of the substituent at the amine. (Figure presented.).
Synthesis of the tetracyclic core skeleton of the lundurines by a gold-catalyzed cyclization
Ferrer, Catalina,Escribano-Cuesta, Ana,Echavarren, Antonio M.
experimental part, p. 9015 - 9020 (2009/12/24)
The 1H-azocino[5,4-b]indole skeleton of the lundurines has been prepared by the 8-endo-dig cyclization of an alkynylindole using AuCl3 or other gold complexes as catalysts.
Nicholas reactions of amines
Roth, Klaus-Dieter,Mueller, Utz
, p. 2919 - 2922 (2007/10/02)
An efficient synthesis of mono- and bispropargylated tertiary amines is described, using the Nicholas reaction with primary and secondary amines as nucleophiles.
