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Synthesis and Properties of 7-Acetyl-8-aryl-9-cyano-3-hydroxy-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

7-Acetyl-8-aryl-2-(1-chloro-2-hydroxy-3-propyl)thio-9-cyano-6-methyl-1,4-dihydropyridines were obtained by treatment of 1,4-dihydropyridine-2(3H)-thiones with epichlorohydrin in the presence of sodium bicarbonate. When treated with NaOMe, these compounds are readily intramolecularly alkylated with formation of 7-acetyl-8-aryl-3-hydroxy-9-cyano-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b]-[1,3]thiazines. We have studied amination of 2-(1-chloro-2-hydroxy-3-propyl)thio-1,4-dihydropyridines and acylation of 3-hydroxy-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines.

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REFERENCES

  1. A. Krauze, R. Verhe, and G. Duburs, Khim. Geterotsikl. Soedin., 139 (1994).

  2. L. Baumane, A. Krauze, L. Cernova, L. Sile, G. Duburs, and J. Stradins, Khim. Geterotsikl. Soedin., 1808 (2003).

  3. A. Krauze, L. Baumane, L. Sile, L. Cernova, M. Vilums, R. Vitolina, G. Duburs, and J. Stradins, Khim. Geterotsikl. Soedin., 1022 (2004).

  4. A. San Feliciano, E. Caballero, P. Puebla, J. A. P. Pereira, J. Gras, and C. Valenti, Eur. J. Med. Chem., 27, 527 (1992).

    Google Scholar 

  5. A. A. Krauze, J. E. Pelcher, Z. A. Kalme, and G. J. Duburs, Khim. Geterotsikl. Soedin., 1694 (1984).

  6. A. A. Krauze, R. O. Vitolina, M. R. Romanova, and G. J. Duburs, Khim.-Farm. Zh., 22, 548 (1988).

    CAS  Google Scholar 

  7. B. M. Khadilkar, V. R. Mestha, and S. R. Bhayade, Indian J. Chem., 33B, 451 (1994).

    CAS  Google Scholar 

  8. V. Cecchetti, F. Schiaffella, O. Tabarrini, and A. Fravolini, Bioorg. Med. Chem. Lett., 10, 465 (2000).

    Article  CAS  Google Scholar 

  9. V. V. Kastrone, R. O. Vitolina, and G. J. Duburs, Khim.-Farm. Zh., 24, No.6, 14 (1990).

    Google Scholar 

  10. N. Rojstaczer and D. J. Triggle, Cardiovascular Drug Reviews, 12, 70 (1994).

    CAS  Google Scholar 

  11. A. A. Krauze, E. E. Liepins, J. E. Pelcher, Z. A. Kalme, and G. J. Duburs, Khim. Geterotsikl. Soedin., 1504 (1984).

  12. A. A. Krauze, E. E. Liepins, J. E. Pelcher, Z. A. Kalme, and G. J. Duburs, Khim. Geterotsikl. Soedin., 95 (1985).

  13. A. Krauze, R. Verhe, and G. Duburs, Latv. J. Chem., 94 (1996).

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

    A. Krauze, L. Sile, R. Danne & G. Duburs

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  1. A. Krauze
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  2. L. Sile
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  3. R. Danne
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  4. G. Duburs
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1394–1399, September, 2005.

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Krauze, A., Sile, L., Danne, R. et al. Synthesis and Properties of 7-Acetyl-8-aryl-9-cyano-3-hydroxy-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines. Chem Heterocycl Compd 41, 1189–1193 (2005). https://doi.org/10.1007/s10593-005-0302-5

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  • DOI: https://doi.org/10.1007/s10593-005-0302-5

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