Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines

Dimitra Kontokosta, Daniel S. Mueller, Dong-Liang Mo, Wiktoria H. Pace, Rachel A. Simpson and Laura L. Anderson
Beilstein J. Org. Chem. 2015, 11, 2097–2104. https://doi.org/10.3762/bjoc.11.226

Supporting Information

Supporting Information File 1: Experimental part.
Format: PDF Size: 6.6 MB Download

Cite the Following Article

Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
Dimitra Kontokosta, Daniel S. Mueller, Dong-Liang Mo, Wiktoria H. Pace, Rachel A. Simpson and Laura L. Anderson
Beilstein J. Org. Chem. 2015, 11, 2097–2104. https://doi.org/10.3762/bjoc.11.226

How to Cite

Kontokosta, D.; Mueller, D. S.; Mo, D.-L.; Pace, W. H.; Simpson, R. A.; Anderson, L. L. Beilstein J. Org. Chem. 2015, 11, 2097–2104. doi:10.3762/bjoc.11.226

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

  • Tanaka, K.; Yoshida, M.; Yamamoto, A.; Hashimoto, Y.; Morita, N.; Tamura, O. Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst. Advanced Synthesis & Catalysis 2023, 365, 1419–1424. doi:10.1002/adsc.202300110
  • Alonso, L.; Shevlin, M.; Alshreimi, A. S.; Reidl, T. W.; Wink, D. J.; Anderson, L. L. Substituent and Solvent Effect Studies of N-Alkenylnitrone 4π Electrocyclizations. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202300551. doi:10.1002/chem.202300551
  • Talukdar, H.; Gogoi, D.; Phukan, P. Chemoselective Chan-Lam and reductive nitroarene coupling of boronic acid using an octahedral Ni-DMAP complex as catalyst. Tetrahedron 2023, 132, 133251. doi:10.1016/j.tet.2023.133251
  • Zou, N.; Liu, Z.; Yan, G.; Wang, Y.; Liang, C.; Mo, D. DBU‐Promoted 6π‐Azaelectrocyclization and Hydrogen‐Migration to Prepare 6‐Alkyl Pyridine N‐Oxides from N‐Vinyl‐α,β‐Unsaturated Nitrones. Advanced Synthesis & Catalysis 2022, 364, 1671–1676. doi:10.1002/adsc.202200066
  • Chandra, P. Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals. ChemistrySelect 2021, 6, 10274–10322. doi:10.1002/slct.202103035
  • Zhao, J.; Huang, B.-Q.; Zhu, B.-C.; Ma, X.-P.; Mo, D.-L. Visible Light Promoted Chan-Lam Reaction and Cycloaddition to Prepare Chromeno[4,3-c]isoxazolidines in One-Pot Reaction. Advanced Synthesis & Catalysis 2021, 363, 4575–4581. doi:10.1002/adsc.202100448
  • Zhang, G.; Alshreimi, A. S.; Alonso, L.; Antar, A.; Yu, H.; Islam, S. M.; Anderson, L. L. Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis. Angewandte Chemie 2021, 133, 13199–13207. doi:10.1002/ange.202101511
  • Zhang, G.; Alshreimi, A. S.; Alonso, L. C.; Antar, A.; Yu, H.-C.; Islam, S. M.; Anderson, L. L. Nitrone and Alkyne Cascade Reactions for Regio‑ and Diastereoselective 1‑Pyrroline Synthesis. Angewandte Chemie (International ed. in English) 2021, 60, 13089–13097. doi:10.1002/anie.202101511
  • Brown, A. T.; Downer-Riley, N. K. Copper catalysis for pyridines and pyrimidines. Copper in N-Heterocyclic Chemistry; Elsevier, 2021; pp 115–159. doi:10.1016/b978-0-12-821263-9.00004-7
  • Zou, N.; Qin, X.; Wang, Z.; Shi, W.; Mo, D. Advances on the Synthesis and Application of α,β-Unsaturated Nitrones. Chinese Journal of Organic Chemistry 2021, 41, 4535. doi:10.6023/cjoc202109007
  • Nekvinda, J.; Santos, W. L. Copper Catalysis in Organic Synthesis; Wiley, 2020; pp 23–49. doi:10.1002/9783527826445.ch3
  • Liao, J.-Y.; Wu, Q.-Y.; Lu, X.; Ning, Z.; Pan, C.-X.; Liang, C.; Su, G.-F.; Mo, D.-L. A copper-catalyzed diastereoselective O-transfer reaction of N-vinyl-α,β-unsaturated nitrones with ketenes into γ-lactones through [5 + 2] cycloaddition and N–O bond cleavage. Green Chemistry 2019, 21, 6567–6573. doi:10.1039/c9gc01811e
  • West, M. J.; Fyfe, J. W. B.; Vantourout, J. C.; Watson, A. J. B. Mechanistic Development and Recent Applications of the Chan-Lam Amination. Chemical reviews 2019, 119, 12491–12523. doi:10.1021/acs.chemrev.9b00491
  • Erdoğan, T. Synthesis, characterization, DFT and molecular docking studies for novel 1,5-diphenylpenta-1,4-dien-3-one O -benzyl oximes. Journal of the Iranian Chemical Society 2019, 16, 2243–2255. doi:10.1007/s13738-019-01697-0
  • Murahashi, S.-I.; Imada, Y. Synthesis and Transformations of Nitrones for Organic Synthesis. Chemical reviews 2019, 119, 4684–4716. doi:10.1021/acs.chemrev.8b00476
  • Ning, Z.; Jiao, J.-W.; Yu, F.; Pan, C.-X.; Liang, C.; Su, G.-F.; Mo, D.-L. Iron(III)/Copper(II)-Cocatalyzed Cycloaddition/[3,3]-Rearrangement/N–O Bond Cleavage To Prepare Polysubstituted Pyrrolizines from N-Vinyl-α,β-Unsaturated Nitrones and Activated Alkynes. Organic letters 2019, 21, 481–485. doi:10.1021/acs.orglett.8b03767
  • Zhiwen, Z.; Wei, H.; Xiao, K.; Cheng, B.; Zhai, H.; Li, Y. Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids. Angewandte Chemie (International ed. in English) 2018, 58, 1148–1152. doi:10.1002/anie.201811812
  • Zhao, Z.; Wei, H.; Xiao, K.; Cheng, B.; Zhai, H.; Li, Y. Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids. Angewandte Chemie 2018, 131, 1160–1164. doi:10.1002/ange.201811812
  • Ma, X.-P.; Li, L.-G.; Hongping, Z.; Du, M.; Liang, C.; Mo, D.-L. Formal [7 + 2] Cycloaddition of Arynes with N-Vinyl-α,β-Unsaturated Nitrones: Synthesis of Benzoxazonines and Their N–O Bond Cleavage. Organic letters 2018, 20, 4571–4574. doi:10.1021/acs.orglett.8b01761
  • Feng, J.; Ma, P.-J.; Zeng, Y.-M.; Xu, Y.-J.; Lu, C.-D. Construction of α-methoxyimidoyl ketonitrones via phosphite-mediated addition of α-keto N-tert-butanesulfinyl imidates to nitrosoarenes. Chemical communications (Cambridge, England) 2018, 54, 2882–2885. doi:10.1039/c8cc00345a
Other Beilstein-Institut Open Science Activities