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Monatshefte für Chemie / Chemical Monthly

, Volume 119, Issue 2, pp 253–262 | Cite as

Beiträge zur Chemie von Pyrazolyalkinen

2. Mitteilung über Pyrazole
  • Gottfried Heinisch
  • Wolfgang Holzer
  • Claudia Obala
Organische Chemie Und Biochemie

On the chemistry of pyrazolylalkines; pyrazoles II

Abstract

Palladium-catalyzed reactions of 1-benzoyl-4-iodopyrazole (2a) with monosubstituted acetylenes3a,3b and3c in triethylamine solution provide convenient access to the cross-coupled products4a,4b and4c. The 4-ethinylpyrazoles5a and7 obtained after methanolytic removal of the protecting groups are transformed conveniently into the ketones6a and8 by means of Hg(II)-mediated hydratation.

Keywords

1-Benzoyl-4-ethinylpyrazoles 4-Ethinylpyrazoles Pd-assisted cross-coupling reactions 4-Pyrazolylketones 

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Literatur

  1. [1]
    1. Mitt.:Heinisch G, Holzer W, Huber T (1987) Arch Pharm (Weinheim) 320: 1267Google Scholar
  2. [2]
    Vasilevskii SF,Shvartsberg MS,Kotlyarevskii IL (1971) Izv Akad Nauk SSSR Ser Khim: 1764, Chem Abstr (1971) 75: 151724p;Vasilevskii SF,Slabuka PA,Izyumov EG,Shvartsberg MS,Kotlyarevskii IL (1972) Izv Akad Nauk SSSR Ser Khim: 2524, Chem Abstr (1973) 78: 71993x;Shvartsberg MS,Vasilevskii SF,Kotlyarevskii IL (1972) Khim Atsetilena Tr Ves Konf 3rd 1968: 134, Chem Abstr (1973) 79: 42402u;Finar IF,Okoh EJ (1973) J Chem Soc Perkin Trans I: 2008;Shvatsberg MS,Vasilevskii SF,Anisimova TV,Gerasimov VA (1981) Izv Akad Nauk SSSR Ser Khim: 1342, Chem Abstr (1981) 95: 150523yGoogle Scholar
  3. [3]
    Tolf BR, Dahlbom R, Theorell H, Akeson A (1982) Acta Chem Scand B 36: 101Google Scholar
  4. [4]
    Buchner E, Fritsch M (1892) Liebigs Ann Chem 273: 262Google Scholar
  5. [5]
    Tschesche R, Schäfer H (1955) Chem Ber 88: 87Google Scholar
  6. [6]
    Jäger V,Viehe HG (1977) Houben Weyl 5/2a: 727;Meerwein J (1965) Houben Weyl 6/3: 234;Stetter H (1973) Houben Weyl 7/2a: 819Google Scholar
  7. [7]
    Reppe W (1955) Liebigs Ann Chem 596: 73Google Scholar
  8. [8]
    Ames DE,Bull D,Takundwa C (1981) Synthesis: 364Google Scholar
  9. [9]
    Elguero J (1984) in:Katritzky AR, Rees CW (ed) Comprehensive heterocyclic chemistry, vol 5. Pergamon Press, Oxford, p 182, und dort zitierte LiteraturGoogle Scholar
  10. [10]
    Heinisch G, Waglechner R (1984) J Heterocycl Chem 21: 1727Google Scholar
  11. [11]
    Birkofer L, Franz M (1972) Chem Ber 105: 1759;Zbiral E, Bauer E (1972) Tetrahedron 28: 4189Google Scholar

Copyright information

© Springer-Verlag 1988

Authors and Affiliations

  • Gottfried Heinisch
    • 1
  • Wolfgang Holzer
    • 1
  • Claudia Obala
    • 1
  1. 1.Institut für Pharmazeutische ChemieUniversität WienWienÖsterreich

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