Abstract:
Palladium(O)-catalysed cross-coupling reactions of 4-methoxy-6-methyl-3-chlorozinco-2-pyrone with aryl- and vinyl-halides and 4-bromo-2-pyrone with organozinc compounds such as aryl-, heteroaryl- and ethynyl-zinc chlorides produce 3- and 4-substituted 2H-pyran-2-ones in moderate to good yields.
Document Type:
Article
Language: English
Citation:
V. N. Kalinin, O. S. Shilova, D. S. Okladnoy, H. Schmidhammer, “Palladium-catalysed synthesis of 3- and 4-substituted 2H-pyran-2-ones”, Mendeleev Commun., 6:6 (1996), 244–245
Linking options:
https://www.mathnet.ru/eng/mendc4997
https://www.mathnet.ru/eng/mendc/v6/i6/p244
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Lixuan Liang, Kai Wang, Chengming Bian, Liming Ling, Zhiming Zhou, “4‐Nitro‐3‐(5‐tetrazole)furoxan and Its Salts: Synthesis, Characterization, and Energetic Properties”, Chemistry A European J, 19:44 (2013), 14902
Ian J. S. Fairlamb, Ciara T. O'Brien, Zhenyang Lin, King Chung Lam, “Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone”, Org. Biomol. Chem., 4:7 (2006), 1213
Ian J.S. Fairlamb, Adam F. Lee, Faidjiba E.M. Loe-Mie, Elina H. Niemelä, Ciara T. O'Brien, Adrian C. Whitwood, “Halogenated-2-pyrones in Sonogashira cross-coupling: limitations, optimisation and consequences for GC analysis of Pd-mediated reactions”, Tetrahedron, 61:41 (2005), 9827
Rafael Chinchilla, Carmen Nájera, Miguel Yus, “Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry”, Chem. Rev., 104:5 (2004), 2667
Matteo Biagetti, Fabio Bellina, Adriano Carpita, Stéphane Viel, Luisa Mannina, Renzo Rossi, “Selective Synthesis of 5,6-Disubstituted 3-Methyl-2(2H)-pyranones and 6-Substituted 3-Methyl-2(2H)-pyranones, Including Fusalanipyrone and Gibepyrone A”, Eur. J. Org. Chem., 2002:6 (2002), 1063
Silvia Cerezo, Marcial Moreno-Mañas, Roser Pleixats, “3-Aryl and 5-aryl-4-methoxy-6-methyl-2H-pyran-2-ones by Suzuki cross-coupling reactions of 3- and 5-halogeno-4-methoxy-6-methyl-2H-pyran-2-ones”, Tetrahedron, 54:27 (1998), 7813
V. N. KALININ, O. S. SHILOVA, D. S. OKLADNOY, H. SCHMIDHAMMER, “ChemInform Abstract: Palladium‐Catalyzed Synthesis of 3‐ and 4‐Substituted 2H‐Pyran‐2‐ones.”, ChemInform, 28:15 (1997)
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