Abstract
A new method for the synthesis of 2-unsubstituted and 2-substituted 3-(N-arylcarbamoyl)-chromones by the reaction of 3-dimethylamino-1-(2-hydroxyaryl)prop-2-en-1-ones with arylisocyanates has been proposed.
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A. Gomes, O. Neuwirth, M. Freitas, D. Couto, D. Ribeiro, A. G. P. R. Figueiredo, A. M. S. Silva, R. S. G. R. Seixas, D. C. G. A. Tomé, J. A. S. Cavaleiro, E. Fernandes, J. L. F. C. Lima, Bioorg. Med. Chem., 2009, 17, 7218.
A. Gaspar, T. Silva, M. Yanez, D. Vina, F. Orallo, F. Ortuso, E. Uriarte, S. Alcaro, F. Borges, J. Med. Chem., 2011, 54, 5165.
A. Gaspar, E. Uriarte, F. Borges, J. Reis, S. Kachler, S. Paoletta, K. N. Klotz, S. Moro, Biochem. Pharm., 2012, 84, 21.
J. Josey, E. S. Inks, X. Wen, C. Chou, C. James,J. Med. Chem., 2013, 56, 1007.
N. Milhazes, A. Melo, M. Natália, D. S. Cordeiro, F. Ortuso, S. Alcaro, F. Borges, ChemMedChem, 2011, 6, 628.
J. Reis, N. Manzella, F. Cagide, J. Mialet-Perez, E. Uriarte, A. Parini, F. Borges, C. Binda, J. Med. Chem., 2018, 61, 4203.
G. Singh, N. Gupta, V. Gupta, M. P. S. Ishar, Tetrahedron Lett., 2017, 58, 2456.
C. Papaneophytou, P. Alexiou, A. Papakyriakou, E. Ntougkos, K. Tsiliouka, A. Maranti, F. Liepouri, A. Strongilos, A. Mettou, E. Couladouros, E. Eliopoulos, E. Douni, G. Kollias, G. Kontopidis, MedChemComm, 2015, 6, 1196.
D. Yu. Demin, K. A. Myannik, P. A. Ermolich, M. M. Krayushkin, V. N. Yarovenko, Mendeleev Commun., 2018, 28, 485.
S. Mkrtchyan, V. O. Iaroshenko, S. Dudkin, A. Gevorgyan, M. Vilches-Herrera, G. Ghazaryan, D. M. Volochnyuk, D. Ostrovskyi, Z. Ahmed, A. Villinger, V. Y. Sosnovskikh, P. Langer, Org. Biomol. Chem., 2010, 8, 5280.
D. Ostrovskyi, V. Iaroshenko, I. Ali, S. Mkrtchyan, A. Villinger, P. Langer, A. Tolmachev, Synthesis, 2011, 1, 133.
T. Patonay, A. Vasas, A. Kiss-Szikszai, A. M. S. Silva, J. A. S. Cavaleiro, Aust. J. Chem., 2010, 63, 1582.
S. Elias, Am. J. App. Sci., 2012, 9, 103.
J. Joussot, A. Schoenfelder, L. Larquetoux, M. Nicolas, J. Suffert, G. Blond, Synthesis, 2016, 48, 3364.
K. A. Myannik, V. N. Yarovenko, M. M. Krayushkin, K. S. Levchenko, Russ. Chem. Bull., 2014, 63, 543.
J. Reis, F. Cagide, D. Chavarria, T. Silva, C. Fernandes, A. Gaspar, E. Uriarte, F. Remiao, S. Alcaro, F. Ortuso, J. Med. Chem., 2016, 59, 5879.
А. Fonseca, J. Reis, T. Silva, M. J. Matos, D. Bagetta, F. Ortuso, S. Alcaro, E. Uriarte, F. Borges,J. Med. Chem., 2017, 60, 7206.
L. R. Gomes, J. N. Low, F. Cagide, D. Chavarria, F. Borges, Acta Crystallogr., 2015, 71, 547.
K. Okumura, K. Kondo, T. Oine, I. Inoue, Chem. Pharm. Bull., 1974, 22, 331.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0104–0109, January, 2019.
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Myannik, K.A., Semenova, I.S., Yarovenko, V.N. et al. Synthesis of 3-(N-arylcarbamoyl)chromones from 2-hydroxyarylaminoenones and isocyanates. Russ Chem Bull 68, 104–109 (2019). https://doi.org/10.1007/s11172-019-2423-5
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DOI: https://doi.org/10.1007/s11172-019-2423-5