Abstract
A facile synthetic route to 9,10-dimethyl-9,10-ethanoanthracene-fused heterocycles such as diazoles and quinoxalines is reported. The key intermediate involved is 2,3,6,7-tetraamino-9,10-dimethyl- 9,10-ethanoanthracene. The target molecules have been fully identified by spectral characterizations.
Similar content being viewed by others
REFERENCES
Anthony, J.E., Angew. Chem., Int. Ed., 2008, vol. 47, p. 452. https://doi.org/10.1002/anie.200604045
Fogel, Y., Kastler, M., Wang, Z.H., Andrienko, D., Bodwell, G.J., and Müllen, K., J. Am. Chem. Soc., 2007, vol. 129, p. 11743. https://doi.org/10.1021/ja072521t
Stępień, M., Gońka, E., Żyła, M., and Sprutta, N., Chem. Rev., 2017, vol. 117, p. 3479. https://doi.org/10.1021/acs.chemrev.6b00076
Sun, Y.M., Tan, L., Jiang, S.D., Qian, H.L., Wang, Z.H., Yan, D.W., Di, C.A., Wang, Y., Wu, W.P., Yu, G., Yan, S.K., Wang, C.R., Hu, W.P., Liu, Y.Q., and Zhu, D.B., J. Am. Chem. Soc., 2007, vol. 129, p. 1882. https://doi.org/10.1021/ja068079g
Williams, K.A. and Bielawski, C.W., Chem. Commun., 2010, vol. 46, p. 5166. https://doi.org/10.1039/C0CC01070G
Chen, L., Kim, J., Ishizuka, T., Honsho, Y., Saeki, A., Seki, S., Ihee, H., and Jiang, D., J. Am. Chem. Soc., 2009, vol. 131, p. 7287. https://doi.org/10.1021/ja901357h
Carta, M., Malpass-Evans, R., Croad, M., Rogan, Y., Jansen, J.C., Bernardo, P., Bazzarelli, F., and McKeown, N.B., Science, 2013, vol. 339, p. 303. https://doi.org/10.1126/science.1228032
Abrahams, B.F., FitzGerald, N.J., and Robson, R., Inorg. Chem., 2010, vol. 49, p. 5953. https://doi.org/10.1021/ic1004006
Xie, T.Z., Guo, K., Guo, Z., Gao, W.Y., Wojtas, L., Ning, G.H., Huang, M., Lu, X., Li, J.Y., Liao, S.Y., Chen, Y.S., Moorefield, C.N., Saunders, M.J., Cheng, S.Z.D., Wesdemiotis, C., and Newkome, G.R., Angew. Chem., Int. Ed., 2015, vol. 54, p. 9224. https://doi.org/10.1002/anie.201503609
Ma, P.Y., Liang, F.H., Wang, D., Yang, Q.Q., Yang, Z.Q., Gao, D.J., Yu, Y., Song, D.Q., and Wang, X.H., Dyes Pigm., 2015, vol. 122, p. 224. https://doi.org/10.1016/j.dyepig.2015.06.030
Urakawa, K., Sumimoto, M., Arisawa, M., Matsuda, M., and Ishikawa, H., Angew. Chem., Int. Ed., 2016, vol. 55, p. 7432. https://doi.org/10.1002/anie.201601906
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Zhong, Y., Ujeed, A. & Liu, Q. Synthesis of 9,10-Dimethyl-9,10-ethanoanthracene-Based Diazoles and Quinoxalines. Russ J Org Chem 58, 1895–1901 (2022). https://doi.org/10.1134/S1070428022120193
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022120193