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Synthesis and Reactivity of 2-(Furan-2-yl)benzo[1,2-d:4,3-d′]bis[1,3]thiazole

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Abstract

Acylation of 1,3-benzothiazol-6-amine with furan-2-carbonyl chloride in propan-2-ol gave N-(1,3-benzothiazol-6-yl)furan-2-carboxamide which was converted to the corresponding thioamide by treat­ment with excess P2S5 in anhydrous toluene. The subsequent oxidation with potassium hexacyanoferrate(III) in alkaline medium afforded 2-(furan-2-yl)benzo[1,2-d:4,3-d′]bis[1,3]thiazole which was subjected to electrophilic substitution reactions (bromination, nitration, hydroxymethylation, formylation, acylation). The substituent entered exclusively into the 5-position of the furan ring.

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REFERENCES

  1. Sherman, W.R. and Dickson, D.E., J. Org. Chem., 1962, vol. 27, no. 4, p. 1351. https://doi.org/10.1021/jo01051a053

    Article  CAS  Google Scholar 

  2. Maruyama, T., Kuroki, N., and Konishi, K., Kogyo Kagaku Zasshi, 1965, vol. 68, p. 2428. https://doi.org/10.1246/nikkashi1898.68.12_2428

    Article  CAS  Google Scholar 

  3. Jacobson, P., Ber., 1886, vol. 19, p. 1067. https://doi.org/10.1002/cber.188601901239

    Article  Google Scholar 

  4. Fărcăşan, V. and Makkay, C., Acad. Repub. Pop. Rom., Fil. Cluj, Stud. Cercet. Chim., 1959, vol. 10, p. 145.

    Google Scholar 

  5. Melnikova, E.B., El’chaninov, M.M., Milov, A.A., and Lukyanov, B.S., Chem. Heterocycl. Compd., 2008, vol. 44, p. 1070. https://doi.org/10.1007/S10593-008-0156-8

    Article  CAS  Google Scholar 

  6. Kornilov, M.Yu., Ruban, E.M., Fedchuk, V.N., Starin­skaya, E.V., and Buznik, M.V., Zh. Org. Khim., 1973, vol. 9, p. 2577.

    CAS  Google Scholar 

  7. Denton, D.A. and Suschitzky, H., J. Chem. Soc., 1963, p. 4741. https://doi.org/10.1039/JR9630004741

  8. Gardner, P.D., J. Am. Chem. Soc., 1954, vol. 76, p. 4550. https://doi.org/10.1021/ja01647a011

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Platov South-Russian State Polytechnic University, 346428, Novocherkassk, Russia

    A. A. Aleksandrov, M. M. Elchaninov, D. A. Tishina, Yu. E. Tarakanova & M. L. Shmanovsky

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  1. A. A. Aleksandrov
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  2. M. M. Elchaninov
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  3. D. A. Tishina
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  4. Yu. E. Tarakanova
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  5. M. L. Shmanovsky
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Correspondence to A. A. Aleksandrov.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 4, pp. 583–587 https://doi.org/10.31857/S0514749221040145.

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Aleksandrov, A.A., Elchaninov, M.M., Tishina, D.A. et al. Synthesis and Reactivity of 2-(Furan-2-yl)benzo[1,2-d:4,3-d′]bis[1,3]thiazole. Russ J Org Chem 57, 664–667 (2021). https://doi.org/10.1134/S1070428021040242

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  • DOI: https://doi.org/10.1134/S1070428021040242

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