A number of 1,4-benzoxathiine derivatives was obtained using ring contraction of seven-membered cycle of 3,4-dihydro-2H-1,5-benzoxathiepin-3-ol derivatives. This synthetic approach allowed to obtain the corresponding alkene, alcohol, nitrile, chloride, bromide, azide, and amine.
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Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
Pustenko, A.; Žalubovskis, R. Chem. Heterocycl. Compd. 2017, 53, 1283. [Khim. Geterotsikl. Soedin. 2017, 53, 1283.]
Tarasiuk, T. M.; Shyshkina, O. O. Chem. Heterocycl. Compd. 2016, 52, 999. [Khim. Geterotsikl. Soedin. 2016, 52, 999.]
Tarasiuk, T. M.; Shyshkina, O. O.; Volovenko, Y. M.; Medviediev, V. V.; Volovnenko, T. A.; Shishkin, O. V. Monatsh. Chem. 2015, 146, 1733.
Vacher, B.; Pignier, C.; Létienne, R.; Verscheure, Y.; Le Grand, B. Br. J. Pharmacol. 2009, 156, 214.
Pignier, C.; Rougier, J.-S.; Vié, B.; Culié, C.; Verscheure, Y.; Vacher, B.; Abriel, H.; Le Grand, B. Br. J. Pharmacol. 2010, 161, 79.
Mahfoudh, N.; Marín-Ramos, N. I.; Gil, A. M.; Jiménez, A. I.; Choquesillo-Lazarte, D.; Kawano, D. F.; Campos, J. M.; Cativiela, C. Arabian J. Chem. 2018, 11, 426.
Díaz-Gavilán, M.; Conejo-García, A.; Cruz-López, O.; Núñez, M. C.; Choquesillo-Lazarte, D.; González-Pérez, J. M.; Rodríguez-Serrano, F.; Marchal, J. A.; Aránega, A.; Gallo, M. A.; Espinosa, A.; Campos, J. M. ChemMedChem 2008, 3, 127.
Kimatrai, M.; Conejo-García, A.; Ramírez, A.; Andreolli, E.; Da Silveira-Gomes, A.; García, M. A.; Aránega, A.; Marchal, J. A.; Campos, J. M. ChemMedChem 2011, 6, 1854.
Donald, J. R.; Unsworth, W. P. Chem.–Eur. J. 2017, 23, 8780.
Abdel-Wahab, B. F.; Shaaban, S.; El-Hiti, G. A. Mol. Diversity 2018, 22, 517.
Kirmse, W. Eur. J. Org. Chem. 2002, 2193.
Silva, L. F. Tetrahedron 2002, 58, 9137.
Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523.
García-Rubiño, M. E.; Núñez-Carretero, M. C.; Choquesillo-Lazarte, D.; García-Ruiz, J. M.; Madrid, Y.; Campos, J. M. RSC Adv. 2014, 4, 22425.
García-Rubiño, M. E.; Núñez, M. C.; Gallo, M. A.; Campos, J. M. RSC Adv. 2012, 2, 12631.
Casiraghi, A.; Valoti, E.; Suigo, L.; Artasensi, A.; Sorvillo, E.; Straniero, V. J. Org. Chem. 2018, 83, 13217.
Mühlstädt, M.; Stransky, N.; Seifert, A.; Kleinpeter, E.; Meinhold, H. J. Prakt. Chem. 1978, 320, 113.
Pigini, M.; Brasili, L.; Giannella, M.; Giardina, D.; Gulini, U.; Quaglia, W.; Melchiorre, C. J. Med. Chem. 1988, 31, 2300.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(4/5), 416–420
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Tarasiuk, T.M., Shyshkina, O.O., Potikha, L.M. et al. Cationic ring contraction of seven-membered cycle of 3,4-dihydro-2H-1,5-benzoxathiepine derivatives. Chem Heterocycl Comp 55, 416–420 (2019). https://doi.org/10.1007/s10593-019-02474-w
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DOI: https://doi.org/10.1007/s10593-019-02474-w