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Functionalized N-propargylanabazine derivatives

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Abstract

N-Propargyl derivatives of the alkaloid anabazine with carbonyl, ester, and cyano groups in the side chain were obtained by three-component condensation of anabazine hydrochloride with paraformaldehyde and appropriate terminal alkynes. Decyanoethylation and hydration of the isopropylidene double bond resulted in mono-and dihydroxy derivatives of N-propargyl-anabazines, respectively.

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References

  1. V. F. Kucherov, M. V. Mavrov, A. R. Derzhinskii, Prirodnye poliatsetilenovye soedineniya [Natural Polyacetylene Compounds], Nauka, Moscow, 1972, 391 pp. (in Russian); Modern Acetylenic Chemistry, Eds P. J. Stang, F. Diederich, Wiley-VCH, Weinheim, 1995; A. A. Semenov, Ocherkkhimii prirodnykh soedinenii [An Essay on the Chemistry of Natural Compounds], Nauka, Novosibirsk, 2000, 664 pp. (in Russian); K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem., Int. Ed., 2005, 44, 4442; U. Galm, M. H. Hager, S. G. VanLanen, J. Ju, J. S. Thorson, B. Shen, Chem. Rev., 2005, 105, 739.

    Google Scholar 

  2. P. G. Cozzi, R. Hilgrof, N. Zimmermann, Eur. J. Org. Chem., 2004, 4095; S. T. Diver, A. G. Giessert, Chem. Rev., 2004, 104, 1317; J. Muzart, Tetrahedron, 2005, 61, 9423; L. Zani, C. Bolm, Chem. Commun., 2006, 4263; L. Hintermann, A. Labonne, Synthesis, 2007, 1121; R. Chinchilla, C. Najera, Chem. Rev., 2007, 107, 874.

  3. C. Wei, Z. Li, Chao-Jun Li, Synlett., 2004, 1472; G. W. Kabalka, L. L. Zhou, L. Wang, R. M. Pagni, Tetrahedron, 2006, 62, 857.

    Google Scholar 

  4. M. W. Holladay, M. J. Dart, J. K. Linch, J. Med. Chem., 1997, 40, 4169; T. Kihara, S. Shimohama, Acta Neurobiol. Exp., 2004, 64, 99; L. F. Martin, W. R. Kem, R. Freedman, Psychopharmacology, 2004, 174, 54.

    Article  CAS  Google Scholar 

  5. L. S. Bleicher, N. D. P. Cosford, A. Herbaut, J. S. McCallum, I. A. McDonald, J. Org. Chem., 1998, 63, 1109; D. L. Comins, E. D. Smith, Tetrahedron Lett., 2006, 47, 1449.

    Article  CAS  Google Scholar 

  6. K. E. Schulte, G. Rucker, in Progress Drug Research, Birkhauser Verlag, Basel—Stuttgart, 1970, 14, 387–563; S. V. Anichkov, N. V. Khromov-Borisov, N. A. Zakharova, S. I. Gaft, E. P. Bekhtereva, A. P. Rudenko, Khim.-Farm. Zh., 1976, 10, No. 11, 53 [Pharm. Chem. J. (Engl. Transl.), 1976, 10, 1478].

    Google Scholar 

  7. M. V. Mavrov, S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2007, 1576 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1637].

  8. A. N. Kost, V. G. Yashunskii, Dokl. Akad. Nauk SSSR, 1952, 83, 93 [Chem. Abstr., 1953, 47, 15644]; M. F Shostakovskii, A. S. Atavin, B. A. Trofimov, N. A. Vodbol’skaya, N. K. Gusarova, V. I. Lavrov, Dokl. Akad. Nauk SSSR, 1966, 166, 1381 [Chem. Abstr., 1966, 64, 92854].

    CAS  Google Scholar 

  9. C. A. Buehler, D. E. Pearson, Survey of Organic Synthesis, Wiley-Interscience, New York, 1970; H. Pakdel, S. Sarron, C. Roy, J. Agric. Food Chem., 2001, 49, 4337.

    Google Scholar 

  10. L. Brandsma, Preparative Acetylenic Chemistry (2nd ed.), Amsterdam, Elsevier, 1988.

    Google Scholar 

  11. D. Merkel, Z. Chem., 1969, No. 2, 63.

    Google Scholar 

  12. M. V. Mavrov, E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1993, 2122 [Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 2035].

  13. I. N. Nazarov, G. A. Shvekhgeimer, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1956, 199 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1956, 5].

  14. A. R. Derzhinskii, M. V. Mavrov, V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1965, 1237 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1965, 14].

  15. J. Colonge, R. Gelin, Bull. Soc. Chim. Fr., 1954, 208, 797.

    Google Scholar 

  16. M. V. Mavrov, N. K. Khao, I. M. Vol’pin, M. P. Zabokritskii, E. P. Serebryakov, L. I. Shinyaeva, N. S. Nazarenko, V. N. Burov, Bioorg. Khim., 1986, 12, 961 [Sov. J. Bioorg. Chem. (Engl. Transl.), 1986].

    CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. V. Mavrov & S. G. Zlotin

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  1. M. V. Mavrov
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  2. S. G. Zlotin
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Correspondence to M. V. Mavrov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1860–1865, September, 2009.

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Mavrov, M.V., Zlotin, S.G. Functionalized N-propargylanabazine derivatives. Russ Chem Bull 58, 1921–1926 (2009). https://doi.org/10.1007/s11172-009-0262-5

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  • DOI: https://doi.org/10.1007/s11172-009-0262-5

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