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Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines
Author(s) -
Zaman Manzoor,
Hasan Muhammad,
Peshkov Anatoly A.,
Van Hecke Kristof,
Van der Eycken Erik V.,
Pereshivko Olga P.,
Peshkov Vsevolod A.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901064
Subject(s) - chemistry , trifluoromethanesulfonate , ugi reaction , domino , cationic polymerization , imine , catalysis , combinatorial chemistry , indole test , adduct , aryl , isocyanide , organic chemistry , alkyl
A silver(I) triflate‐catalyzed protocol for the post‐Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3‐alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four‐component Ugi reaction into a two‐step one‐pot transformation.