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Metal-free cyclization of ortho-nitroaryl ynamides and ynamines towards spiropseudoindoxyls

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Abstract
An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.

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Chicago
Marien, Niels, B Narendraprasad Reddy, Freija De Vleeschouwer, Steven Goderis, Kristof Van Hecke, and Guido Verniest. 2018. “Metal-free Cyclization of Ortho-nitroaryl Ynamides and Ynamines Towards Spiropseudoindoxyls.” Angewandte Chemie-international Edition 57 (20): 5660–5664.
APA
Marien, N., Reddy, B. N., De Vleeschouwer, F., Goderis, S., Van Hecke, K., & Verniest, G. (2018). Metal-free cyclization of ortho-nitroaryl ynamides and ynamines towards spiropseudoindoxyls. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 57(20), 5660–5664.
Vancouver
1.
Marien N, Reddy BN, De Vleeschouwer F, Goderis S, Van Hecke K, Verniest G. Metal-free cyclization of ortho-nitroaryl ynamides and ynamines towards spiropseudoindoxyls. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2018;57(20):5660–4.
MLA
Marien, Niels, B Narendraprasad Reddy, Freija De Vleeschouwer, et al. “Metal-free Cyclization of Ortho-nitroaryl Ynamides and Ynamines Towards Spiropseudoindoxyls.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57.20 (2018): 5660–5664. Print.
@article{8581224,
  abstract     = {An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.},
  author       = {Marien, Niels and Reddy, B Narendraprasad and De Vleeschouwer, Freija and Goderis, Steven and Van Hecke, Kristof and Verniest, Guido},
  issn         = {1433-7851},
  journal      = {ANGEWANDTE CHEMIE-INTERNATIONAL EDITION},
  language     = {eng},
  number       = {20},
  pages        = {5660--5664},
  title        = {Metal-free cyclization of ortho-nitroaryl ynamides and ynamines towards spiropseudoindoxyls},
  url          = {http://dx.doi.org/10.1002/anie.201800340},
  volume       = {57},
  year         = {2018},
}

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