Abstract
cis-5-Arylpyrrolidine-2-carboxylates, obtained by 1,3-dipolar cycloaddition reactions from glycine aryl aldimines and vinyl sulfones, undergo oxidative aromatization under the action of Mn(IV) oxide to form the corresponding 5-arylpyrrole-2-carboxylates in high yields. Factors responsible for the retention of the sulfonyl substituent in the pyrrole backbone were determined.
REFERENCES
O’Malley, D.P., Li, K., Maue, M., Zografos, A.L., and Baran, P.S., J. Am. Chem. Soc., 2007, vol. 129, p. 4762. https://doi.org/10.1021/ja069035a
Wang, X., Gao, Y., Ma, Z., Rodriguez, R.A., Yu, Z.-X., and Chen, C., Org. Chem. Front., 2015, vol. 2, p. 978. https://doi.org/10.1039/C5QO00165J
Hughes, C.C., Prieto-Davo, A., Jensen, P.R., and Fenical, W., Org. Lett., 2008, vol. 10, p. 629. https://doi.org/10.1021/ol702952n
Bhardwaj, V., Gumber, D., Abbot, V., Dhimana, S., and Sharmaa, P., RSC Adv., 2015, vol. 5, p. 15233. https://doi.org/10.1039/C4RA15710A
Mohamed, M.S. and Fathallah, S.S., Mini Rev. Org. Chem., 2014, vol. 11, p. 477. https://doi.org/10.2174/1570193X113106660018
Bellina, F. and Rossi, R., Tetrahedron, 2006, vol. 62, p. 7213. https://doi.org/10.1016/j.tet.2006.05.024
Sharma, V., Bhatia, P., Alam, O., Naim, M.J., Nawaz, F., Sheikh, A.A., and Jhadoi, M., Bioorg. Chem., 2019, vol. 89, ID 103007. https://doi.org/10.1016/j.bioorg.2019.103007
Dhameja, M. and Gupta, P., Eur. J. Med. Chem., 2019, vol. 176, p. 343. https://doi.org/10.1016/j.ejmech.2019.04.025
Masci, D., Hind, C., Toscani, A., Clifford, M., Coluccia, A., Conforti, I., Touitou, M., Memdouh, S., Wei, X., La Regina, G., Silvestri, R., Sutton, J.M., and Castagnolo, D., Eur. J. Med. Chem., 2019, vol. 178, p. 500. https://doi.org/10.1016/j.ejmech.2019.05.087
Raimondi, M.V., Listro, R., Cusimano, M.G., La Francaa, M., Faddetta, T., Galloa, G., Schillaci, D., Collina, S., Leonchiks, A., and Barone, G., Bioorg. Med. Chem., 2019, vol. 27, p. 721. https://doi.org/10.1016/j.bmc.2019.01.010
Knorr, L., Ber. Chem. Ges., 1884, vol. 17, p. 1635. https://doi.org/10.1002/cber.18840170220
Paal, C., Ber. Chem. Ges., 1885, vol. 18, p. 367. https://doi.org/10.1002/cber.18850180175
Hantzsch, A., Ber. Chem. Ges., 1890, vol. 23, p. 1474. https://doi.org/10.1002/cber.189002301243
Leonardi, M., Estévez, V., Villacampa, M., and Menéndez, J.C., Synthesis, 2019, vol. 51, p. 816. https://doi.org/10.1055/s-0037-1610320
Tejedor, D. González-Cruz, D., García-Tellado, F., Marrero-Tellado, J.J., and Rodríguez, M.L., J. Am. Chem. Soc., 2004, vol. 126, p. 8390. https://doi.org/10.1021/ja047396p
Cyr, D.J., Martin, N., and Arndtsen, B.A., Org. Lett., 2007, vol. 9, p. 449. https://doi.org/10.1021/ol062773j
Balakrishna, A., Aguiar, A., Sobral, P.J.M., Wani, M.Y., Silva, J.A., and Sobraldoi, A.J.F.N., Catal. Rev. Sci. Eng., 2019, vol. 61, p. 449. https://doi.org/10.1080/01614940.2018.1529932
Hati, S., Holzgrabe, U., and Sen, S., Beilstein J. Org. Chem., 2017, vol. 13, p. 1670. https://doi.org/10.3762/bjoc.13.162
Feng, C., Yan, Y., Zhang, Z., Xua, K., and Wang, Z., Org. Biomol. Chem., 2014, vol. 12, p. 4837. https://doi.org/10.1039/c4ob00708e
Bonnaud, B. and Bigg, C.H., Synthesis, 1994, vol. 5, p. 465. https://doi.org/10.1055/s-1994-25500
Liu, Y., Hu, H., Wang, X., Zhi, S., Kan, Y., and Wang, C., J. Org. Chem., 2017, vol. 82, p. 4194. https://doi.org/10.1021/acs.joc.7b00180
Cheruku, S.R., Padmanilayam, M.P., and Vennerstrom, J.L., Tetrahedron Lett., 2003, vol. 44, p. 3701. https://doi.org/10.1016/S0040-4039(03)00740-8
Blaney, P., Grigg, R., Rankovic, Z., Thornton-Pett, M., and Xu, J., Tetrahedron, 2002, vol. 58, p. 1719. https://doi.org/10.1016/S0040-4020(02)00029-7
Petrov, P.S., Kalyazin, V.A., and Somov, N.V., Russ. J. Org. Chem., 2021, vol. 57, p. 170. https://doi.org/10.31857/S0514749221020063
Kudryavtsev, K.V., Ivantcova, P.M., Churakov, A.V., and Vasin, V.A., Tetrahedron Lett., 2012, vol. 53, p. 4300. https://doi.org/10.1016/j.tetlet.2012.05.160
Casas, J., Grigg, R., Najera, C., and Sansano, J.M., Eur. J. Org. Chem., 2001, vol. 123, p. 1971. https://doi.org/10.1002/1099-0690(200105)2001:10
Arrieta, A., Otaegui, D., Zubia, A., Cossío, F.P., DíazOrtiz, A., de la Hoz, A., Herrero, M.A., Prieto, P., FocesFoces, C., Pizarro, L.J., and Arriortua, M.I., J. Org. Chem., 2007, vol. 72, p. 4313. https://doi.org/10.1021/jo062672z
Goldman, I.M., J. Org. Chem., 1969, vol. 34, p. 3289. https://doi.org/10.1021/jo01263a015
Nájera, C., Baldó, B., and Yus, M., J. Chem. Soc., Perkin Trans. 1, 1988, p. 1029. https://doi.org/10.1039/P19880001029
Fu, J., He, Z., Wang, H., Liang, W., and Guo, C., J. Min. Sci. Technol., 2010, vol. 20, p. 877. https://doi.org/10.1016/S1674-5264(09)60299-4
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218
Hübschle, C.B., Sheldrick, G.M., and Dittrich, B., J. Appl. Crystallogr., 2011, vol. 44, p. 1281. https://doi.org/10.1107/S0021889811043202
Clark, R.C. and Reid, J.S., Acta Crystallogr. Sect. A, 1995, vol. 51, p. 887. https://doi.org/10.1107/S0108767395007367
Farrugia, L.J., J. Appl. Crystallogr., 2012, vol. 45, p. 849. https://doi.org/10.1107/S0021889812029111
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Kostryukov, S.G., Kalyazin, V.A., Petrov, P.S. et al. 5-Arylpyrrolidine-2-carboxylic Acid Derivatives as Precursors in the Synthesis of Sulphonyl-substituted Pyrroles. Russ J Org Chem 60, 281–293 (2024). https://doi.org/10.1134/S1070428024020143
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DOI: https://doi.org/10.1134/S1070428024020143