Supporting Information
Supporting Information File 1: Experimental details on the synthesis of all DHPMs 5 and intermediate 6a, full characterization data as well as 1H and 13C NMR spectra of all products 5 and 6a. | ||
Format: PDF | Size: 1.2 MB | Download |
Cite the Following Article
Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea
Jie-Ping Wan, Yunfang Lin, Kaikai Hu and Yunyun Liu
Beilstein J. Org. Chem. 2014, 10, 287–292.
https://doi.org/10.3762/bjoc.10.25
How to Cite
Wan, J.-P.; Lin, Y.; Hu, K.; Liu, Y. Beilstein J. Org. Chem. 2014, 10, 287–292. doi:10.3762/bjoc.10.25
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
- Shuhaib, Z. A.; Hussein, K. A.; Ismael, S. M. Synthesis of New Pyrimidine Derivatives, Study of Anti-Сancer Activity, Structural Properties, and Molecular Docking. Russian Journal of General Chemistry 2023, 93, 1171–1180. doi:10.1134/s1070363223050183
- Torabi, M.; Yarie, M.; Baghery, S.; Zolfigol, M. A. Recent advances in catalytic synthesis of pyridine derivatives. Recent Developments in the Synthesis and Applications of Pyridines; Elsevier, 2023; pp 503–580. doi:10.1016/b978-0-323-91221-1.00002-6
- Sánchez-Sancho, F.; Escolano, M.; Gaviña, D.; Csáky, A. G.; Sánchez-Roselló, M.; Díaz-Oltra, S.; Del Pozo, C. Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions. Pharmaceuticals (Basel, Switzerland) 2022, 15, 948. doi:10.3390/ph15080948
- Zhou, M.; Wang, Y.; Lin, X.; Wan, J.; Wen, C. Specific TLR4 Blocking Effect of a Novel 3,4-Dihydropyrimidinone Derivative. Frontiers in pharmacology 2021, 11, 624059. doi:10.3389/fphar.2020.624059
- Nishimura, Y. Development of Efficient Synthetic Method for Tautomeric Dihydropyrimidines and Analysis of Their Functionality. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 2021, 141, 151–161. doi:10.1248/yakushi.20-00182
- Nishimura, Y.; Kikuchi, H.; Kubo, T.; Nakakita, I.; Oguni, M.; Ohta, M.; Arai, R.; Yuan, B.; Sunaga, K.; Cho, H. Synthesis of novel 6-unsubstituted 2-aminodihydropyrimidines by Sc(OTf)3-mediated amination and their antiproliferative effect on HL-60 cells. Tetrahedron Letters 2021, 65, 152760. doi:10.1016/j.tetlet.2020.152760
- Meng, D.; Xie, Y.; Peng, Q.; Wang, J. NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones. Organic letters 2020, 22, 7635–7639. doi:10.1021/acs.orglett.0c02832
- Nishimura, Y.; Kikuchi, H.; Kubo, T.; Gokurakuji, Y.; Nakamura, Y.; Arai, R.; Yuan, B.; Sunaga, K.; Cho, H. Synthesis of 6-unsubstituted 2-oxo, 2-thioxo, and 2-amino-3,4-dihydropyrimidines and their antiproliferative effect on HL-60 cells. Tetrahedron Letters 2020, 61, 151967. doi:10.1016/j.tetlet.2020.151967
- Moumita, S.; Asish, R. D. Nanocrystalline ZnO: A Competent and Reusable Catalyst for the Preparation of Pharmacology Relevant Heterocycles in the Aqueous Medium. Current Green Chemistry 2020, 7, 53–104. doi:10.2174/2213346107666200218122718
- Flores-Morales, V.; Ayala-Medrano, E. D.; García-Elías, J.; Martinez-Fierro, M. L.; Marquez, E.; Mora, J. R. Understanding the Lack of Reactivity of 2,4-Dihydroxybenzaldehyde Towards the Biginelli Adduct Using Density Functional Theory Molecular Modeling. Processes 2019, 7, 521. doi:10.3390/pr7080521
- Kumar, L. R.; Panduranga, V.; Vishwanatha, T. M.; Shekharappa; Sureshbabu, V. V. Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates. Organic & biomolecular chemistry 2018, 16, 2258–2263. doi:10.1039/c8ob00239h
- Nematpour, M.; Rezaee, E.; Jahani, M.; Tabatabai, S. A. Highly regioselective, base-catalyzed, biginelli-type reaction of aldehyde, phenylacetone and urea/thiourea kinetic vs. thermodynamic control. Journal of Sulfur Chemistry 2017, 39, 151–163. doi:10.1080/17415993.2017.1402332
- Khatri, C. K.; Potadar, S. M.; Chaturbhuj, G. U. A reactant promoted solvent free synthesis of 3,4-dihydropyrimidin-2(1H)-thione analogues using ammonium thiocyanate. Tetrahedron Letters 2017, 58, 1778–1780. doi:10.1016/j.tetlet.2017.03.070
- Gao, Y.; Hu, C.; Wan, J.-P.; Wen, C. Metal-free cascade reactions of aldehydes and primary amines for the synthesis of 1,3,4-trisubstituted pyrroles. Tetrahedron Letters 2016, 57, 4854–4857. doi:10.1016/j.tetlet.2016.09.063
- Wan, J.-P.; Gao, Y. Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines. Chemical record (New York, N.Y.) 2016, 16, 1164–1177. doi:10.1002/tcr.201500296
- Khan, I.; Ibrar, A.; Abbas, N.; Saeed, A. One-pot access to a privileged library of six membered nitrogenous heterocycles through multi-component cascade approach. Research on Chemical Intermediates 2015, 42, 5147–5196. doi:10.1007/s11164-015-2354-1
- Hu, D.; Liu, Y.; Wan, J.-P. An organocatalytic multi-molecular cascade reaction for the synthesis of acetate functionalized 1,4-dihydropyridines. Tetrahedron 2015, 71, 6094–6098. doi:10.1016/j.tet.2015.06.101
- Zhang, Y.; Liu, Y.; Wan, J.-P. Copper-catalyzed three-component reactions of phenols, acyl chlorides and Wittig reagents for the synthesis of β-aryloxyl acrylates. New Journal of Chemistry 2015, 39, 1567–1569. doi:10.1039/c4nj02010c
- Wan, J.-P.; Lin, Y.; Jing, Y.; Xu, M.; Liu, Y. Selectivity tunable divergent synthesis of 1,4- and 1,2-dihydropyridines via three-component reactions. Tetrahedron 2014, 70, 7874–7880. doi:10.1016/j.tet.2014.09.002
- Kour, G.; Gupta, M.; Paul, S.; Rajnikant; Gupta, V. K. SiO2–CuCl2: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Journal of Molecular Catalysis A: Chemical 2014, 392, 260–269. doi:10.1016/j.molcata.2014.05.022