An efficient synthesis of dihydrofurans and furans by a reaction between 1,3-dicarbonyl compounds and ethyl bromopyruvate, ethyl 2-chloroacetoacetate, or 3-chloroacetylacetone in the presence of ammonium acetate in aqueous ethanol is described. When the reaction was performed with a phenacyl bromide, O-alkylation of 1,3-dicarbonyl compounds occurred without cyclization.
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Mross, G.; Holtz, E.; Langer, P. J. Org. Chem. 2006, 71, 8045.
Dunlop, A. P.; Hurd, C. D. J. Org. Chem. 1950, 15, 1160.
Calter, M. A.; Zhu, C. Org. Lett. 2002, 4, 205.
(a) Cantlon, I. J. ; Cocker, W.; Mcmurry, T. B. H. Tetrahedron 1961, 15, 46. (b) Ranu, B. C.; Adak, L.; Banerjee, S. Tetrahedron Lett. 2008, 49, 4613. (c) Calter, M. A.; Philips, R. M.; Flaschenriem, C. J. Am. Chem. Soc. 2005, 127, 14566. (d) Jin, Y.; Liu, X. Y.; Jing, L. L.; He, W.; Sun, X. L.; Zhang, S. Y. Chirality 2007, 19, 386. (e) Shafiee, A.; Shekarchi, M.; Ellahiyan, F.; Akbarzadeh, T. J. Heterocycl. Chem. 2003, 40, 427.
Chen, H.; Jiang, R.; Wang, Q. F.; Sun, X. L.; Luo, J.; Zhang, S. Y. Chin. Chem. Lett. 2010, 21, 167.
Calter, M. A.; Korotkov, A. Org. Lett. 2011, 13, 6328.
Calter, M. A.; Korotkov, A. Org. Lett. 2015, 17, 1385.
Sinha, D.; Biswas, A.; Singh, V. K. Org. Lett. 2015, 17, 3302.
Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301.
Kubo, I.; Lee, Y.-W.; Balogh-Nair, V.; Nakanishi, K.; Chapya, A. J. Chem. Soc., Chem. Commun. 1976, 22, 949.
Schulte, G.; Scheuer, P. J.; McConnell, O. Helv. Chim. Acta 1980, 63, 2159.
Yavari, I.; Sabbaghan, M. Synth. Commun. 2007, 37, 1791.
Yavari, I.; Sirouspour, M. ; Souri, S.; Nasiri, F.; Djahaniani, H. Mendeleev Commun. 2005, 15, 120.
Yavari, I.; Hosseini, N.; Moradi, L.; Mirzaei, A. Tetrahedron Lett. 2008, 49, 4239.
Stetter, H.; Lauterbach, R. Chem. Ber. 1960, 93, 603.
Ibata, T.; Miyauchi, K.; Nakata, S. Bull. Chem. Soc. Jpn. 1979, 52, 3467.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(3), 161–164
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Ghazvini, M., Shahvelayati, A.S., Sabri, A. et al. Synthesis of furan and dihydrofuran derivatives via Feist–Benary reaction in the presence of ammonium acetate in aqueous ethanol. Chem Heterocycl Comp 52, 161–164 (2016). https://doi.org/10.1007/s10593-016-1854-2
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DOI: https://doi.org/10.1007/s10593-016-1854-2