Silver(I) Triflate-Catalyzed Protocol for the Post-Ugi Synthesis of Spiroindolines

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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Zaman M.1 , Hasan M.1 , Peshkov A.A.2 , Van Hecke K. , Van Der Eycken E.V. , Pereshivko O.P.1, 2 , Peshkov V.A.1, 2, 6
Wiley-VCH Verlag
  • 1 College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
  • 2 Department of Chemistry, School of Science and Technology, Nazarbayev University, 53 Kabanbay Batyr Ave, Block 7, Nur-Sultan, 010000, Kazakhstan
  • 3 XStruct, Department of Chemistry, Ghent University, Krijgslaan 281-S3, Ghent, B-9000, Belgium
  • 4 Laboratory of Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 5 Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, Moscow, 117198, Russian Federation
  • 6 The Environment and Resource Efficiency Cluster (EREC), Nazarbayev University, Nur-Sultan, Kazakhstan
Ключевые слова
Domino reactions; Multicomponent reactions; Nitrogen heterocycles; Silver catalysis; Spiro compounds
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