Abstract
Aldol addition of acyclic and cyclic ketones to 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones afforded the corresponding 1-substituted 1-hydroxy-4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones. The short-time reduction of 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones with sodium tetrahydridoborate gave 1-hydroxy-4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones.
Similar content being viewed by others
REFERENCES
Zhou, J., Jiang, X., He, S., Jiang, H., Feng, F., Liu, W., Qu, W., and Sun, H., J. Med. Chem., 2019, vol. 62, p. 8881. https://doi.org/10.1021/acs.jmedchem.9b00017
Song, F., Li, Zh., Bian, Y., Huo, X., Fang, J., Shao, L., and Zhou, M., Arch. Pharm., 2020, vol. 353, article ID e2000143. https://doi.org/10.1002/ardp.202000143
Munson, H.R., US Patent no. 4198414, 1980; Ref. Zh., Khim., 1981, no. 20146P.
Leschcheva, E.V., Medvedeva, S.M., and Shikhaliev, Kh.S., Zh. Org. Farm. Khim., 2014, vol. 12, p. 15. https://doi.org/10.24959/ophcj.14.798
Matesic, L., Locke, J.M., Vine, K., Ranson, M., Bremner, J.B., and Skropeta, D., Tetrahedron, 2012, vol. 68, p. 6810. https://doi.org/10.1016/j.tet.2012.06.049
Novichikhina, N.P., Shestakov, A.S., Potapov, A.Yu., Kosheleva, E.A., Shatalov, G.V., Verezhnikov, V.N., Vandyshev, D.Yu., Ledeneva, I.V., and Shikhaliev, Kh.S., Russ. Chem. Bull., Int. Ed., 2020, vol. 69, p. 787. https://doi.org/10.1007/s11172-020-2834-3
Medvedeva, S.M., Potapov, A.Yu., Gribkova, I.V., Katkova, E.V., Sulimov, V.B., and Shikhaliev, Kh.S., Pharm. Chem. J., 2018, vol. 51, p. 975. https://doi.org/10.1007/s11094-018-1726-4
Novichikhina, N., Ilin, I., Tashchilova, A., Sulimov, A., Kutov, D., Ledenyova, I., Krysin, M., Shikhaliev, Kh., Gantseva, A., Gantseva, E., Podoplelova, N., and Sulimov, V., Molecules, 2020, vol. 25, article no. 1889. https://doi.org/10.3390/molecules25081889
Sulimov, V.B., Gribkova, I.V., Kochugaeva, M.P., Katkova, E.V., Sulimov, A.V., Kutov, D.C., Shikhaliev, Kh.S., Medvedeva, S.M., Krysin, M.Yu., Sinauridze, E.I., and Ataullakhanov, F.I., BioMed Res. Int., 2015, vol. 2015, article ID 120802. https://doi.org/10.1155/2015/120802
Novichikhina, N.P., Skoptsova, A.A., Shestakov, A.S., Potapov, A.Yu., Kosheleva, E.A., Kozaderov, O.A., Ledenyova, I.V., Podoplelova, N.A., Panteleev, M.A., and Shikhaliev, Kh.S., Russ. J. Org. Chem., 2020, vol. 56, p. 1550. https://doi.org/10.1134/S1070428020090080
Peddibhotla, S., Curr. Bioact. Compd., 2009, vol. 5, p. 20. https://doi.org/10.2174/157340709787580900
Yasuda, D., Takahashi, K., Ohe, T., Nakamura, S., and Mashino, T., Bioorg. Med. Chem., 2013, vol. 21, p. 7709. https://doi.org/10.1016/j.bmc.2013.10.021
Céspedes, C.L., Alarcon, J., Valdez-Morales, M., and Paredes-López, O., Z. Naturforsch., Teil C, 2009, vol. 64, p. 759. https://doi.org/10.1515/znc-2009-9-1024
Prathima, P.S., Rajesh, P., Rao, J.V., Kailash, U.S., Sridhar, B., and Rao, M.M., Eur. J. Med. Chem., 2014, vol. 84, p. 155. https://doi.org/10.1016/j.ejmech.2014.07.004
Codding, P.W., Lee, T.A., and Richardson, J.F., J. Med. Chem., 1984, vol. 27, p. 649. https://doi.org/10.1021/jm00371a016
Kawasaki, T., Nagaoka, M., Satoh, T., Okamoto, A., Ukon, R., and Ogawa, A., Tetrahedron, 2004, vol. 60, p. 3493. https://doi.org/10.1016/j.tet.2004.02.031
Tripathi, R.K.P., Krishnamurthy, S., and Ayyannan, S.R., ChemMedChem, 2016, vol. 11, p. 119. https://doi.org/10.1002/cmdc.201500443
Mazaheri, F., Saatluo, B.E., Baradarani, M.M., and Joule, J.A., J. Heterocycl. Chem., 2017, vol. 54, p. 147. https://doi.org/10.1002/jhet.2555
Saatluo, B.E., Baradarani, M.M., and Joule, J.A., J. Heterocycl. Chem., 2018, vol. 55, p. 1176. https://doi.org/10.1002/jhet.3150
Chen, G., Wang, Y., He, H., Gao, S., Yang, X., and Hao, X., Heterocycles, 2006, vol. 68, p. 2327. https://doi.org/10.3987/COM-06-10856
Kon, K., Kohari, Y., and Murata, M., Tetrahedron Lett., 2019, vol. 60, p. 415. https://doi.org/10.1016/j.tetlet.2018.12.049
Nagle, A.A., Reddy, S.A., Bertrand, H., Tajima, H., Dang, T.-M., Wong, S.-Ch., Hayes, J.D., Wells, G., and Chew, E.-H., ChemMedChem, 2014, vol. 9, p. 1763. https://doi.org/10.1002/cmdc.201402038
Thakur, R.K., Joshi, P., Upadhyaya, K., Singh, K., Sharma, J., Shukla, S.K., Tripathi, R., and Tripathi, R.P., Eur. J. Med. Chem., 2019, vol. 162, p. 448. https://doi.org/10.1016/j.ejmech.2018.11.008
Liu, X.-W., Yang, J., Wang, G.-L., Gong, Y., Feng, T.-T., Liu, X.-L., Cao, Y., Zhou, Y., and Yuan, W.-Ch., J. Heterocycl. Chem., 2018, vol. 55, p. 353. https://doi.org/10.1002/jhet.3027
Chen, W.-B., Liao, Y.-H., Du, X.-L., Zhang, X.-M., and Yuan, W.-Ch., Green Chem., 2009, vol. 11, p. 1465. https://doi.org/10.1039/b906684e
Zhao, H., Meng, W., Yang, Zh., Tian, T., Sheng, Zh., Li, H., Song, X., Zhang, Y., Yang, S., and Li, B., Chin. J. Chem., 2014, vol. 32, p. 417. https://doi.org/10.1002/cjoc.201400166
Kimura, J., Subba Reddy, U.V., Kohari, Y., Seki, Ch., Mawatari, Y., Uwai, K., Okuyama, Y., Kwon, E., Tokiwa, M., Takeshita, M., Iwasa, T., and Nakano, H., Eur. J. Org. Chem., 2016, vol. 2016, p. 3748. https://doi.org/10.1002/ejoc.201600414
Ogasawara, A., Subba Reddy, U.V., Seki, Ch., Okuyama, Y., Uwai, K., Tokiwa, M., Takeshita, M., and Nakano, H., Tetrahedron: Asymmetry, 2016, vol. 27, p. 1062. https://doi.org/10.1016/j.tetasy.2016.08.013
Hata, H., Shimizu, S., Hattori, Sh., and Yamada, H., J. Org. Chem., 1990, vol. 55, p. 4377. https://doi.org/10.1021/jo00301a032
Mandal, T., Jana, S., and Dash, J., Eur. J. Org. Chem., 2017, vol. 2017, p. 4972. https://doi.org/10.1002/ejoc.201700887
Sonderegger, O.J., Bürgi, Th., Limbach, L.K., and Baiker, A., J. Mol. Catal. A: Chem., 2004, vol. 217, p. 93. https://doi.org/10.1016/j.molcata.2004.02.018
Lee, H.S., Kim, K.H., Kim, Y.M., and Kim, J.N., Bull. Korean Chem. Soc., 2010, vol. 31, p. 1761. https://doi.org/10.5012/bkcs.2010.31.6.1761
Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
ACKNOWLEDGMENTS
The IR and mass spectra were recorded using the research facilities of the joint scientific equipment center at the Voronezh State University.
Funding
This study was performed under financial support by the Russian Science Foundation (project no. 18-74-10097-P).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Additional information
Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1393–1402 https://doi.org/10.31857/S0514749221100049.
Rights and permissions
About this article
Cite this article
Novichikhina, N.P., Shestakov, A.S., Skoptsova, A.A. et al. Synthesis of New 1-Hydroxy-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one Derivatives. Russ J Org Chem 57, 1592–1599 (2021). https://doi.org/10.1134/S1070428021100043
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021100043