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Synthesis and permethylation of methyl 5-(2-chloropyridin-3-yl)pentanoates

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Chemistry of Heterocyclic Compounds Aims and scope

Two methyl 5-(2-chloropyridin-3-yl)pentanoates were prepared by condensation of 1,3-bis(silyloxy)-1,3-butadienes with 2-chloropyridine-3-carboxylic acid chloride. The permethylation of the products resulted in two completely different products, depending on the substitution pattern of the 1,3,5-tricarbonyl moiety.

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References

  1. (a) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380. (b) Koskinen, A. M. P.; Karisalmi, K. Chem. Soc. Rev. 2005, 34, 677.

  2. (a) Barrett, A. G. M.; Carr, R. A. E.; Finch, M. A. W.; Florent, J.-C.; Richardson, G.; Walshe, N. D. A. J. Org. Chem. 1986, 51, 4254. (b) Barrett, A. G. M.; Morris, T. M.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1980, 2272.

  3. (a) Harris, T. M.; Harris, C. M. Tetrahedron 1977, 33, 2159. (b) Gilbreath, S. G.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 6172.

  4. Langer, P. Synthesis 2002, 441.

  5. (a) Rahn, T.; Nguyen, V. T. H.; Dang, T. H. T.; Ahmed, Z.; Methling, K.; Lalk, M.; Fischer, C.; Spannenberg, A.; Langer, P. J. Org. Chem. 2007, 72, 1957. (b) Rahn, T.; Dang, T. H. T.; Spannenberg, A.; Fischer, C.; Langer, P. Org. Biomol. Chem. 2008, 6, 3366. (c) Langer, P.; Schneider, T.; Stoll, M. Chem.–Eur. J. 2000, 6, 3204.

  6. (a) Reim, S.; Michalik, D.; Weisz, K.; Xiao, Z.; Langer, P. Org. Biomol. Chem. 2008, 6, 3079. (b) Erfle, S.; Reim, S.; Michalik, D.; Jiao, H.; Langer, P. Eur. J. Org. Chem. 2011, 4367.

  7. Murin, B.; Riedl, W.; Risse, K. H.; Scheublein, M. Chem. Ber. 1959, 92, 2033.

    Article  CAS  Google Scholar 

  8. Erfle, S.; Rahn, T.; Bendrath, F.; Baumann, W.; Michalik, D.; Jiao, H.; Spannenberg, A.; Börner, A.; Langer, P. Tetrahedron 2011, 67, 8780.

    Article  CAS  Google Scholar 

  9. Rahn, T.; Bendrath, F.; Hein, M.; Baumann, W.; Jiao, H.; Börner, A.; Villinger, A.; Langer, P. Org. Biomol. Chem. 2011, 9, 5172.

    Article  CAS  Google Scholar 

  10. Bendrath, F.; Falodun, A.; Abilov, Z. A.; Villinger, A.; Langer, P. J. Heterocycl. Chem. 2014, 51, 835.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institut für Chemie, Universität Rostock, 3a Albert Einstein St, 18059, Rostock, Germany

    Franziska Bendrath & Peter Langer

  2. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, 29a Albert Einstein St, 18059, Rostock, Germany

    Peter Langer

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  1. Franziska Bendrath
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  2. Peter Langer
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Correspondence to Peter Langer.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1146–1148

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Bendrath, F., Langer, P. Synthesis and permethylation of methyl 5-(2-chloropyridin-3-yl)pentanoates. Chem Heterocycl Comp 57, 1146–1148 (2021). https://doi.org/10.1007/s10593-021-03033-y

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  • DOI: https://doi.org/10.1007/s10593-021-03033-y

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