Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides?
New Journal of Chemistry Pub Date: 2020-02-14 DOI: 10.1039/C9NJ06438A
Abstract
An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.
Recommended Literature
- [1] An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. WoodEnergy Environ. Sci., 2018,11, 2784-2812 10.1039/C8EE01085D
- [2] Aluminium complexes with thio-phosphorus ligands: syntheses and characterisations of [Al2(CyPS3)2(CyPHS2)2] and [Al(S2PPh2)3]? Robert P. Davies,Maria A. Giménez,Laura Patel,Andrew J. P. WhiteDalton Trans., 2008, 5705-5707 10.1039/B813427H
- [3] An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency? Green Chem., 2017,19, 1268-1277 10.1039/C6GC03280J
- [4] An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S? Rongning Liang,Tanji Yin,Ruiqing Yao,Wei QinRSC Adv., 2016,6, 73308-73312 10.1039/C6RA14461F
- [5] An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction? Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin JinJ. Mater. Chem. C, 2020,8, 192-200 10.1039/C9TC05297F
- [6] An intramolecular tryptophan-condensation approach for peptide stapling? Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. JohannesOrg. Biomol. Chem., 2018,16, 389-392 10.1039/C7OB02667F
- [7] An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu ChenRSC Adv., 2015,5, 100775-100782 10.1039/C5RA21508K
- [8] An antimonate pyrochlore (H1.23Sr0.45SbO3.48) for photocatalytic oxidation of benzene: effective oxygen usage and excellent activity? Jing Chen,Yu Shao,Danzhen LiJ. Mater. Chem. A, 2017,5, 937-941 10.1039/C6TA08652G
- [9] An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane? Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. YesteJ. Mater. Chem. A, 2019,7, 8993-9003 10.1039/C8TA11672E
- [10] An investigation into the origin of variations in photovoltaic performance using D–D–π–A and D–A–π–A triphenylimidazole dyes with a copper electrolyte? Govind ReddyMol. Syst. Des. Eng., 2021,6, 779-789 10.1039/D1ME00073J
Journal Name:New Journal of Chemistry
research_products
-
CAS no.: 89640-58-4