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Synthesis of Fused Heterocycles Based on 1-Amino-1H-tetrazole-5-thiol and α,β-Unsaturated Aldehydes

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Abstract

8-Phenyltetrazolo[5,1-b][1,3,4]thiadiazepine was obtained as a result of intermolecular cyclization of 1-amino-1H-tetrazole-5-thiol and 3-phenyl-2-propynal. The reaction of α-bromocinnamaldehyde with 1-amino-1H-tetrazole-5-thiol led to the formation of 7-benzylidene-7H-tetrazolo[5,1-b][1,3,4]thiadiazine. An effective method was developed for the synthesis of 1-[(3-phenylprop-2-yn-1-yl)amino]-1H-tetrazole-5-thiol, a key intermediate in the possible synthesis of 7-benzylidene-6,7-dihydro-5H-tetrazolo[5,1-b][1,3,4]thiadiazine.

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REFERENCES

  1. Popova, E.A., Trifonov, R.E., and Ostrovskii, V.A., Russ. Chem. Rev., 2019, vol. 88, no. 6, p. 644. https://doi.org/10.1070/RCR4864

    Article  CAS  Google Scholar 

  2. Eftekhar, M., Eshghi, H., Rahimizadeh, M.M. Bakavoli, M., and Saberi, S., J. Chem. Res., 2014, vol. 38, no. 6, p. 365. https://doi.org/10.3184/174751914X14001496962946

    Article  CAS  Google Scholar 

  3. Igei, M., Bakavoli, M., Shiri, A., Ebrahimpour, Z., Bazizollahi, H., Beyzaei, H., and Moghaddam-Manesh, M., J. Chem. Res., 2016, vol. 40, no. 10, p. 628. https://doi.org/10.3184/174751916X14742893137631

    Article  CAS  Google Scholar 

  4. Eshghi, H., Rahimizadeh, M., Saberi, S., Abnous, Kh., and Bakavoli, M., J. Chem. Res., 2013, vol. 37, no. 9, p. 553. https://doi.org/10.3184/174751913X13738978141695

    Article  CAS  Google Scholar 

  5. Kulikov, A.S., Epishina, M.A., Fershtat, L.L., Romanova, A.A., and Makhova, N.N., Tetrahedron Lett., 2017, vol. 58, no. 48, p. 3998. https://doi.org/10.1016/j.tetlet.2017.09.014

    Article  CAS  Google Scholar 

  6. Skryl’nikova, M.A., Khramchikhin, A.V., and Krivchun, M.N., Russ. J. Gen. Chem., 2017, vol. 87, no. 6, p. 1321. https://doi.org/10.1134/S1070363217060329

    Article  Google Scholar 

  7. Melnikova, Y.V., Roh, J., Kuneš, J., Artamonova, T.V, and Zevatskii, Y.E., Tetrahedron Lett., 2017, vol. 58, no. 40, p. 3842. https://doi.org/10.1016/j.tetlet.2017.08.058

    Article  CAS  Google Scholar 

  8. Myznikov, L.V., Melnikova, Yu.V., Baichurin, R.I., Artamonova, T.V., and Zevatskii, Yu.E., Russ. J. Gen. Chem., 2018, vol. 88, no. 2, p. 216. https://doi.org/10.1134/S1070363218020068

    Article  CAS  Google Scholar 

  9. Wang, T., Miao, W., Wu, S., Bing, G., Zhang, X., Qin, Z., Yu, H., Qin, X., and Fang, J., Chin. J. Chem., 2011, vol. 29, no. 5, p. 959. https://doi.org/10.1002/cjoc.201190196

    Article  CAS  Google Scholar 

  10. CrysAlisPro Software system, version 1.171.36.39. Rigaku Oxford Diffraction, Oxford, UK, 2013.

  11. Sheldrick, G.M., Acta Cryst. (A), 2015, vol. 71, p. 3. https://doi.org/

    Google Scholar 

  12. Sheldrick, G.M., Acta Cryst. (C), 2015, vol. 71, p. 3. https://doi.org/

    Google Scholar 

  13. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, no. 2, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    Yu. S. Gurenkova, V. A. Ostrovsky, M. A. Skrylnikova & A. V. Khramchikhin

  2. St. Petersburg State University, 199034, St. Petersburg, Russia

    I. V. Kornyakov

Authors
  1. Yu. S. Gurenkova
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  2. I. V. Kornyakov
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  3. V. A. Ostrovsky
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  4. M. A. Skrylnikova
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  5. A. V. Khramchikhin
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Correspondence to A. V. Khramchikhin.

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Gurenkova, Y.S., Kornyakov, I.V., Ostrovsky, V.A. et al. Synthesis of Fused Heterocycles Based on 1-Amino-1H-tetrazole-5-thiol and α,β-Unsaturated Aldehydes. Russ J Gen Chem 90, 1202–1206 (2020). https://doi.org/10.1134/S1070363220070051

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  • DOI: https://doi.org/10.1134/S1070363220070051

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