Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

Jing Sun, Hong Gao, Qun Wu and Chao-Guo Yan
Beilstein J. Org. Chem. 2012, 8, 1839–1843. https://doi.org/10.3762/bjoc.8.211

Supporting Information

Experimental details and detailed spectroscopic data including crystallographic data (CIF) of all new compounds are available as Supporting Information. Single crystal data for compound 1c (CCDC 890916) have been deposited in the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK (Fax: +44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk).

Supporting Information File 1: General experimental methods and characterization of compounds.
Format: PDF Size: 919.7 KB Download
Supporting Information File 2: X-ray crystallographic data of 1c.
Format: CIF Size: 17.0 KB Download

Cite the Following Article

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
Jing Sun, Hong Gao, Qun Wu and Chao-Guo Yan
Beilstein J. Org. Chem. 2012, 8, 1839–1843. https://doi.org/10.3762/bjoc.8.211

How to Cite

Sun, J.; Gao, H.; Wu, Q.; Yan, C.-G. Beilstein J. Org. Chem. 2012, 8, 1839–1843. doi:10.3762/bjoc.8.211

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

  • de Fátima, Â.; Fernandes, S. A.; Ferreira de Paiva, W.; de Freitas Rego, Y. The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines. Synthesis 2022, 54, 3162–3179. doi:10.1055/a-1794-8355
  • Muthukrishnan, I.; Sridharan, V.; Menéndez, J. C. Progress in the Chemistry of Tetrahydroquinolines. Chemical reviews 2019, 119, 5057–5191. doi:10.1021/acs.chemrev.8b00567
  • Hajighasemi, H.; Yazdani-Elah-Abadi, A.; Shams, N. An Efficient and Green Stereoselective Synthesis of Functionalized 3-Indol-3-yl-oxoindolin-3-yl-3-acrylates via Nano-Fe3O4-Promoted One-Pot Four-Component Domino Reactions. Polycyclic Aromatic Compounds 2017, 40, 76–87. doi:10.1080/10406638.2017.1355326
  • Vasconcelos, S. N. S.; da Silva, V. H. M.; Braga, A. A. C.; Shamim, A.; Souza, F. B.; Pimenta, D. C.; Stefani, H. A. 3‐Alkenyltyrosines Accessed by Suzuki–Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions. Asian Journal of Organic Chemistry 2017, 6, 913–920. doi:10.1002/ajoc.201700154
  • Marzaro, G.; Via, L. D.; García-Argáez, A. N.; Via, M. D.; Chilin, A. Novel benzoquinoline derivatives via unpredicted condensation of ethyl propiolate and naphthylamines: Synthesis and topoisomerase inhibition activity. Bioorganic & medicinal chemistry letters 2016, 26, 4875–4878. doi:10.1016/j.bmcl.2016.09.031
  • Yaragorla, S.; Saini, P. L.; Pareek, A.; Almansour, A. I.; Arumugam, N. A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives promoted by Ca(OTf)2. Tetrahedron Letters 2016, 57, 2034–2038. doi:10.1016/j.tetlet.2016.03.098
  • Zhang, J.; Yang, W.-J.; Sun, J.; Yan, C.-G. Convenient Synthesis of Functionalized 6‐Styryl‐1,4,5,6‐tetrahydropyridines through a Domino [2+2+2] Cycloaddition Reaction. European Journal of Organic Chemistry 2015, 2015, 7571–7582. doi:10.1002/ejoc.201501052
  • Gao, H.; Sun, J.; Yan, C.-G. Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate. Beilstein journal of organic chemistry 2013, 9, 2934–2939. doi:10.3762/bjoc.9.330
  • Zhang, L.-L.; Sun, J.; Yan, C.-G. One‐pot Sequential Reaction for the Synthesis of Polysubstituted 3‐(3‐Nitro‐2‐phenylchroman‐4‐yl)‐3‐arylaminoacrylates. Chinese Journal of Chemistry 2013, 31, 1546–1550. doi:10.1002/cjoc.201300547
  • Sun, J.; Zhang, L.-L.; Yan, C.-G. Facile construction of 1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizines via one-pot three-component reactions of tryptamines, propiolate, and α,β-unsaturated aromatic aldehydes or ketones. Tetrahedron 2013, 69, 5451–5459. doi:10.1016/j.tet.2013.04.100
Other Beilstein-Institut Open Science Activities