Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

Amit Kumar, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar and Erik V. Van der Eycken
Beilstein J. Org. Chem. 2013, 9, 2097–2102. https://doi.org/10.3762/bjoc.9.246

Supporting Information

Supporting Information File 1: Experimental section.
Format: PDF Size: 1.6 MB Download

Cite the Following Article

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines
Amit Kumar, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar and Erik V. Van der Eycken
Beilstein J. Org. Chem. 2013, 9, 2097–2102. https://doi.org/10.3762/bjoc.9.246

How to Cite

Kumar, A.; Vachhani, D. D.; Modha, S. G.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Beilstein J. Org. Chem. 2013, 9, 2097–2102. doi:10.3762/bjoc.9.246

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Bhoraniya, R. B.; Modha, S. G. Propargyl Amines: Versatile Building Blocks in Post-Ugi Transformations. ChemistryOpen 2023, 12, e202200223. doi:10.1002/open.202200223
  • Lindman, J.; Gopalan, G.; Palo-Nieto, C.; Brandt, P.; Gising, J.; Larhed, M. Diastereoselective Synthesis of N-Methylspiroindolines by Intramolecular Mizoroki-Heck Annulations. ACS omega 2022, 7, 32525–32535. doi:10.1021/acsomega.2c04111
  • Stahlberger, M.; Steinlein, O.; Adam, C. R.; Rotter, M.; Hohmann, J.; Nieger, M.; Köberle, B.; Bräse, S. Fluorescent annulated imidazo[4,5-c]isoquinolines via a GBB-3CR/imidoylation sequence - DNA-interactions in pUC-19 gel electrophoresis mobility shift assay. Organic & biomolecular chemistry 2022, 20, 3598–3604. doi:10.1039/d2ob00372d
  • Manavi, B.; Tejeneki, H. Z.; Rominger, F.; Armaghan, M.; Frank, W.; Bijanzadeh, H. R.; Balalaie, S. Copper(I)-Catalyzed Intramolecular Cyclization of o-Propargyloxy Diketopiperazines to Access Diverse Diazabicyclic and Spiro-Diketopiperazinochromanes. Advanced Synthesis & Catalysis 2021, 363, 4190–4196. doi:10.1002/adsc.202100432
  • Bag, D.; Sawant, S. D. Heteroarene‐tethered Functionalized Alkyne Metamorphosis. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 27, 1165–1218. doi:10.1002/chem.202002154
  • Tian, G.; Song, L.; Li, Z.; Robeyns, K.; Van Meervelt, L.; Van der Eycken, E. V. A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine. Organic letters 2020, 22, 8441–8445. doi:10.1021/acs.orglett.0c03062
  • Pharande, S. G. Synthesis of Lactams via Isocyanide-Based Multicomponent Reactions. Synthesis 2020, 53, 418–446. doi:10.1055/s-0040-1706297
  • Clarke, A. K.; Rossi-Ashton, J. A.; Taylor, R. J. K.; Unsworth, W. P. Synthesis of polycyclic scaffolds via a gold-catalysed dearomative cyclisation cascade. Tetrahedron 2020, 76, 131392. doi:10.1016/j.tet.2020.131392
  • Sabat, N.; Soualmia, F.; Retailleau, P.; Benjdia, A.; Berteau, O.; Guinchard, X. Gold-Catalyzed Spirocyclization Reactions of N-Propargyl Tryptamines and Tryptophans in Aqueous Media. Organic letters 2020, 22, 4344–4349. doi:10.1021/acs.orglett.0c01370
  • Rossi-Ashton, J. A.; Clarke, A. K.; Taylor, R. J. K.; Unsworth, W. P. Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade. Organic letters 2020, 22, 1175–1181. doi:10.1021/acs.orglett.0c00053
  • Heravi, M. M.; Mohammadkhani, L. Synthesis of various N-heterocycles using the four-component Ugi reaction. Advances in Heterocyclic Chemistry 2020, 131, 351–403. doi:10.1016/bs.aihch.2019.04.001
  • Zaman, M.; Hasan, M.; Peshkov, A. A.; Van Hecke, K.; Van der Eycken, E. V.; Pereshivko, O. P.; Peshkov, V. A. Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines. Advanced Synthesis & Catalysis 2019, 362, 261–268. doi:10.1002/adsc.201901064
  • Modha, S. G.; Pöthig, A.; Dreuw, A.; Bach, T. [6π] Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification, Mechanism, and Scope. The Journal of organic chemistry 2019, 84, 1139–1153. doi:10.1021/acs.joc.8b03144
  • Ranjan, P.; Ojeda, G. M.; Sharma, U. K.; Van der Eycken, E. V. Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 2442–2446. doi:10.1002/chem.201805945
  • Du, X.; Huang, J.; Nechaev, A. A.; Yao, R.; Gong, J.; Van der Eycken, E. V.; Pereshivko, O. P.; Peshkov, V. A. Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones. Beilstein journal of organic chemistry 2018, 14, 2572–2579. doi:10.3762/bjoc.14.234
  • Alyabyev, S. B.; Beletskaya, I. P. Gold as a catalyst. Part II. Alkynes in the reactions of carbon – carbon bond formation. Russian Chemical Reviews 2018, 87, 984–1047. doi:10.1070/rcr4815
  • Sharma, U. K.; Tian, G.; Voskressensky, L. G.; Van der Eycken, E. V. Gold-catalyzed post-MCR transformations towards complex (poly)heterocycles. Drug discovery today. Technologies 2018, 29, 61–69. doi:10.1016/j.ddtec.2018.08.003
  • Nechaev, A. A.; Van Hecke, K.; Zaman, M.; Kashtanov, S.; Ungur, L.; Pereshivko, O. P.; Peshkov, V. A.; Van der Eycken, E. V. Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity. The Journal of organic chemistry 2018, 83, 8170–8182. doi:10.1021/acs.joc.8b00953
  • Lei, J.; Xu, Z.-G.; Tang, D. Y.; Li, Y.; Xu, J.; Li, H.-y.; Zhu, J.; Chen, Z. Z. Acid-Promoted One-Pot Synthesis of Substituted Furan and 6-Methylpyrazin-2(1 H)-one Derivatives via Allene Intermediate Formed in Situ. ACS combinatorial science 2018, 20, 292–297. doi:10.1021/acscombsci.8b00005
  • Ziarani, G. M.; Moradi, R.; Ahmadi, T.; Lashgari, N. Recent advances in the application of indoles in multicomponent reactions. RSC advances 2018, 8, 12069–12103. doi:10.1039/c7ra13321a
Other Beilstein-Institut Open Science Activities