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Silver(I) triflate-catalyzed protocol for the post-ugi synthesis of spiroindolines

(2020) ADVANCED SYNTHESIS & CATALYSIS. 362(1). p.261-268
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Abstract
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.
Keywords
SUPPORTED GOLD NANOPARTICLES, CRAFTS ALLYLIC ALKYLATION, MICHAEL CASCADE REACTION, INTRAMOLECULAR HYDROARYLATION, ASYMMETRIC DEAROMATIZATION, ENANTIOSELECTIVE CONSTRUCTION, IPSO-IODOCYCLIZATION, EFFICIENT SYNTHESIS, CYCLIZATION, INDOLES, Domino reactions, Multicomponent reactions, Nitrogen heterocycles, Silver catalysis, Spiro compounds

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Citation

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MLA
Zaman, Manzoor, et al. “Silver(I) Triflate-Catalyzed Protocol for the Post-Ugi Synthesis of Spiroindolines.” ADVANCED SYNTHESIS & CATALYSIS, vol. 362, no. 1, 2020, pp. 261–68, doi:10.1002/adsc.201901064.
APA
Zaman, M., Hasan, M., Peshkov, A. A., Van Hecke, K., Van der Eycken, E. V., Pereshivko, O. P., & Peshkov, V. A. (2020). Silver(I) triflate-catalyzed protocol for the post-ugi synthesis of spiroindolines. ADVANCED SYNTHESIS & CATALYSIS, 362(1), 261–268. https://doi.org/10.1002/adsc.201901064
Chicago author-date
Zaman, Manzoor, Muhammad Hasan, Anatoly A. Peshkov, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko, and Vsevolod A. Peshkov. 2020. “Silver(I) Triflate-Catalyzed Protocol for the Post-Ugi Synthesis of Spiroindolines.” ADVANCED SYNTHESIS & CATALYSIS 362 (1): 261–68. https://doi.org/10.1002/adsc.201901064.
Chicago author-date (all authors)
Zaman, Manzoor, Muhammad Hasan, Anatoly A. Peshkov, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko, and Vsevolod A. Peshkov. 2020. “Silver(I) Triflate-Catalyzed Protocol for the Post-Ugi Synthesis of Spiroindolines.” ADVANCED SYNTHESIS & CATALYSIS 362 (1): 261–268. doi:10.1002/adsc.201901064.
Vancouver
1.
Zaman M, Hasan M, Peshkov AA, Van Hecke K, Van der Eycken EV, Pereshivko OP, et al. Silver(I) triflate-catalyzed protocol for the post-ugi synthesis of spiroindolines. ADVANCED SYNTHESIS & CATALYSIS. 2020;362(1):261–8.
IEEE
[1]
M. Zaman et al., “Silver(I) triflate-catalyzed protocol for the post-ugi synthesis of spiroindolines,” ADVANCED SYNTHESIS & CATALYSIS, vol. 362, no. 1, pp. 261–268, 2020.
@article{8645651,
  abstract     = {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.},
  author       = {Zaman, Manzoor and Hasan, Muhammad and Peshkov, Anatoly A. and Van Hecke, Kristof and Van der Eycken, Erik V. and Pereshivko, Olga P. and Peshkov, Vsevolod A.},
  issn         = {1615-4150},
  journal      = {ADVANCED SYNTHESIS & CATALYSIS},
  keywords     = {SUPPORTED GOLD NANOPARTICLES,CRAFTS ALLYLIC ALKYLATION,MICHAEL CASCADE REACTION,INTRAMOLECULAR HYDROARYLATION,ASYMMETRIC DEAROMATIZATION,ENANTIOSELECTIVE CONSTRUCTION,IPSO-IODOCYCLIZATION,EFFICIENT SYNTHESIS,CYCLIZATION,INDOLES,Domino reactions,Multicomponent reactions,Nitrogen heterocycles,Silver catalysis,Spiro compounds},
  language     = {eng},
  number       = {1},
  pages        = {261--268},
  title        = {Silver(I) triflate-catalyzed protocol for the post-ugi synthesis of spiroindolines},
  url          = {http://dx.doi.org/10.1002/adsc.201901064},
  volume       = {362},
  year         = {2020},
}

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