Metal-free cyclization of ortho-nitroaryl ynamides and ynamines towards spiropseudoindoxyls
- Author
- Niels Marien, B Narendraprasad Reddy, Freija De Vleeschouwer, Steven Goderis, Kristof Van Hecke (UGent) and Guido Verniest
- Organization
- 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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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8581224
- MLA
- Marien, Niels, et al. “Metal-Free Cyclization of Ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 57, no. 20, 2018, pp. 5660–64, doi:10.1002/anie.201800340.
- 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. https://doi.org/10.1002/anie.201800340
- Chicago author-date
- 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): 5660–64. https://doi.org/10.1002/anie.201800340.
- Chicago author-date (all authors)
- 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. doi:10.1002/anie.201800340.
- 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.
- IEEE
- [1]N. Marien, B. N. Reddy, F. De Vleeschouwer, S. Goderis, K. Van Hecke, and G. Verniest, “Metal-free cyclization of ortho-nitroaryl ynamides and ynamines towards spiropseudoindoxyls,” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 57, no. 20, pp. 5660–5664, 2018.
@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://doi.org/10.1002/anie.201800340}},
volume = {{57}},
year = {{2018}},
}
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