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Potassium 1,1,3,3-Tetracyano-2-[2-(methoxycarbonyl)benzoyl]prop-2-enide in the Synthesis of Spiro-Fused Isobenzofuran Derivatives

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Abstract

Successive treatment of potassium 1,1,3,3-tetracyano-2-(2-(methoxycarbonyl)benzoyl)prop-2-enide with concentrated sulfuric acid and water gave 2-(5′-amino-4′-cyano-3-oxo-3H,3′H-spiro[[2]benzofuran-1,2′-furan]-3′-ylidene)propanedinitrile. The reaction of the title compound with sodium hydroxide, followed by neutralization with sulfuric acid afforded 4′-amino-3,3′,6′-trioxo-2′,3′,5′,6′-tetrahydro-3H-spiro[[2]benzofuran-1,1′-pyrrolo[3,4-c]pyridine]-7′-carbonitrile.

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REFERENCES

  1. Almond-Thynne, J., Han, J., White, A.J.P., Polyzos, A., Parsons, P.J., and Barrett, A.G.M., J. Org. Chem., 2018, vol. 83, p. 6783. https://doi.org/10.1021/acs.joc.8b00794

    Article  CAS  PubMed  Google Scholar 

  2. Zhang, C., Liu, M., Ding, M., Xie, H., and Zhang, F., Org. Lett., 2017, vol. 19, p. 3418. https://doi.org/10.1021/acs.orglett.7b01374

    Article  CAS  PubMed  Google Scholar 

  3. Yahata, K., Ye, N., Ai, Y., Iso, K., and Kishi, Y., Angew. Chem., Int. Ed., 2017, vol. 56, p. 10796. https://doi.org/10.1002/anie.201705523

    Article  CAS  Google Scholar 

  4. Davy, J.A., Moreau, B., Oliver, A.G., and Wulff, J.E., Tetrahedron, 2015, vol. 71, p. 2643. https://doi.org/10.1016/j.tet.2015.03.043

    Article  CAS  Google Scholar 

  5. Nakajima, M., Fuwa, H., and Sasaki, M., Bull. Chem. Soc. Jpn., 2012, vol. 85, p. 948. https://doi.org/10.1246/bcsj.20120152

    Article  CAS  Google Scholar 

  6. Wang, X., Han, Z., Wang, Z., and Ding, K., Angew. Chem., Int. Ed., 2012, vol. 51, p. 936. https://doi.org/10.1002/anie.201106488

    Article  CAS  Google Scholar 

  7. Massen, Z.S., Sarli, V.C., Coutouli-Argyropoulou, E., and Gallos, J.K., Carbohydr. Res., 2011, vol. 346, p. 230. https://doi.org/10.1016/j.carres.2010.12.001

    Article  CAS  PubMed  Google Scholar 

  8. Robinson, J.E. and Brimble, M.A., Chem. Commun., 2005, p. 1560. https://doi.org/10.1039/B418106A

  9. Suenaga, K., Araki, K., Sengoku, T., and Uemura, D., Org. Lett., 2001, vol. 3, p. 527. https://doi.org/10.1021/ol006905z

    Article  CAS  PubMed  Google Scholar 

  10. Izmest’ev, A.N., Gazieva, G.A., and Kravchenko, A.N., Chem. Heterocycl. Compd., 2020, vol. 56, p. 255. https://doi.org/10.1007/s10593-020-02654-z

    Article  CAS  Google Scholar 

  11. Yao, H., Zhou, N., Zhang, Z., Guan, W., Wang, H., and Cheng, H.,Tetrahedron Lett., 2020, vol. 61, article ID 151480. https://doi.org/10.1016/j.tetlet.2019.151480

  12. Zhang, Z.J., Nian, Y., Zhu, Q.F., Li, X.N., Su, J., Wu, X-D., Yang, J., and Zhao, Q.-S., Org. Lett., 2017, vol. 19, p. 4668. https://doi.org/10.1021/acs.orglett.7b02293

    Article  CAS  PubMed  Google Scholar 

  13. Yixizhuoma, Ishikawa, N., Abdelfattah, M.S., and Ishibashi, M.,J. Antibiot., 2017, vol. 70, p. 601. https://doi.org/10.1038/ja.2016.158

    Article  CAS  Google Scholar 

  14. Malpani, Y., Achary, R., Kim, S.Y., Jeong, H.C., Kim, P., Han, S.B., Kim, M., Lee, C.-K., Kim, J.N., and Jung, Y.-S., Eur. J. Med. Chem., 2013, vol. 62, p. 534. https://doi.org/10.1016/j.ejmech.2013.01.015

    Article  CAS  PubMed  Google Scholar 

  15. Zhang, X., Yang, C., Zhang-Negrerie, D., and Du, Y., Chem. Eur. J., 2015, vol. 21, p. 5193. https://doi.org/10.1002/chem.201406393

    Article  CAS  PubMed  Google Scholar 

  16. Karpov, S.V., Kaukov, Ya.S., Grigor’ev, A.A., Nasakin, O.E., Kaukova, O.V., and Tafeenko, V.A., Org. Biomol. Chem., 2016, vol. 14, p. 3758. https://doi.org/10.1039/C6OB00092D

    Article  CAS  PubMed  Google Scholar 

  17. Grigor’ev, A.A., Karpov, S.V., Nasakin, O.E., Tafeenko, V.A., Kayukova, O.V., and Kayukova, Ya.S., Russ. J. Org. Chem., 2018, vol. 54, p. 503. https://doi.org/10.1134/S107042801803020X

    Article  Google Scholar 

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Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 18-33-20120 mol_a_ved).

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Correspondence to Ya. S. Kayukov or O. V. Kayukova.

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Kayukov, Y.S., Karpov, S.V., Grigorʼev, A.A. et al. Potassium 1,1,3,3-Tetracyano-2-[2-(methoxycarbonyl)benzoyl]prop-2-enide in the Synthesis of Spiro-Fused Isobenzofuran Derivatives. Russ J Org Chem 56, 1859–1861 (2020). https://doi.org/10.1134/S1070428020100322

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