Abstract
The 1,3-dipolar cycloaddition reaction of (Z)-1-aryl-2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)ethan-1-one with generated in situ azomethine ylide leads to novel 2′-(arylcarbonyl)-6′,10b′-dihydro-2′H,5′H-dispiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline-3′,3′′-indolin]-2′′-one derivatives in moderate yields. Structures of all products have been characterized by NMR, IR and HRMS spectra, and X-ray crystallographic analysis.
Similar content being viewed by others
REFERENCES
Ryu, H., Seo, J., and Ko, H.M., J. Org. Chem., 2018, vol. 83, p. 14102. https://doi.org/10.1021/acs.joc.8b02117
Coldham, I. and Hufton, R., Chem. Rev., 2005, vol. 105, p. 2765. https://doi.org/10.1021/cr040004c
Yu, J., Shi, F., and Gong, L.Z., Acc. Chem. Res., 2011, vol. 44, p. 1156. https://doi.org/10.1021/ar2000343
Chittchang, M., Batsomboon, P., Ruchirawat, S., and Ploypradith, P., Chem. Med. Chem., 2009, vol. 4, p. 457. https://doi.org/10.1002/cmdc.200800339
Newman, D.J., Mar. Drugs., 2015, vol. 13, p. 1105. https://doi.org/10.3390/md13031105
Shen, L., Yang, X.C., Yang, B., He, Q.J., and Hu, Y., Eur. J. Med. Chem., 2010, vol. 45, p.11. https://doi.org/10.1016/j.ejmech.2009.09.017
Chen, T.L., Patel, A.S., Jain, V., Kuppusamy, R., Lin, Y.W., Hou, M.H., Su, T.L., and Lee, T.C., J. Med. Chem., 2021, vol. 64, p. 12469. https://doi.org/10.1021/acs.jmedchem.0c01733
Anderson, W.K., Heider, A.R., Raju, N., and Yucht, J.A., J. Med. Chem., 1988, vol. 31, p. 2097. https://doi.org/10.1021/jm00119a008
Kamiyama, H., Kubo, Y., Sato, H., Yamamoto, N., Fukuda, T., Ishibashi, F., and Iwao, M., Bioorg. Med. Chem., 2011, vol. 19, p. 7541. https://doi.org/10.1016/j.bmc.2011.10.030
Jossang, A., Jossang, P., Hadi, H.A., Sévenet, T., and Bodo, B., J. Org. Chem., 1991, vol. 56, p. 6527. https://doi.org/10.1021/jo00023a016
James, M.N.G. and Williams, G.J.B., Can. J. Chem., 1972, vol. 50, p. 2407. https://doi.org/10.1139/v72-386
Yu, P. and Cook, J.M., Tetrahedron Lett., 1997, vol. 38, p. 8799. https://doi.org/10.1016/S0040-4039(97)10420-8
Edmondson, S., Danishefsky, S.J., and Rosen, N., J. Am. Chem. Soc., 1999, vol. 121, p. 2147. https://doi.org/10.1021/ja983788i
Yu, B., Yu, D.Q., and Liu, H.M., Eur. J. Med. Chem., 2015, vol. 97, p. 673. https://doi.org/10.1016/j.ejmech.2014.06.056
Yang, Y.T., Zhu, J.F., Liao, G., Xu, H.J., and Yu, B., Curr. Med. Chem., 2018, vol. 25, p. 2233. https://doi.org/10.2174/0929867325666171129131311
Bhaskar, G., Arun, Y., Balachandran, C., Saikumar, C., and Perumal, P.T., Eur. J. Med. Chem., 2012, vol. 51, p. 79. https://doi.org/10.1016/j.ejmech.2012.02.024
Huang, Y., Huang, Y.X., Sun, J., and Yan, C.G., RSC Adv., 2018, vol. 8, p. 23990. https://doi.org/10.1039/C8RA04375B
Tseng, C.H., Chen, Y. R., Tzeng, C.C., Liu, W., Chou, C.K., Chiu, C.C., and Chen, Y.L., Eur. J. Med. Chem., 2016, vol. 108, p. 258. https://doi.org/10.1016/j.ejmech.2015.11.031
Stępień, M., Gońka, E., Żyła, M., and Sprutta, N., Chem. Rev., 2017, vol. 117, p. 3479. https://doi.org/10.1021/acs.chemrev.6b00076
Schepetkin, I.A., Kirpotina, L.N., Khlebnikov, A.I., Hanks, T.S., Kochetkova, I., Pascual, D.W., Jutila, M.A., and Quinn, M.T., Mol. Pharmacol., 2012, vol. 81, p. 832. https://doi.org/10.1124/mol.111.077446
Ji, L., Zhou, Y., Yu, Q., Fang, Y., Jiang, Y., Zhao, Y., Yuan, C., and Xie, W., J. Mol. Struc., 2021, vol. 1227, p. 129406. https://doi.org/10.1016/j.molstruc.2020.129406
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Yan, JL., Wu, YW. Synthesis of Dispiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo-[2,1-a]isoquinoline-3′,3′′-indolin]-2′′-one Derivatives via Cycloaddition Reactions. Russ J Gen Chem 91 (Suppl 1), S131–S136 (2021). https://doi.org/10.1134/S107036322202027X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036322202027X