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Chemistry of Heterocyclic Compounds

, Volume 27, Issue 1, pp 71–76 | Cite as

Acetals of lactams and amides. 60. N- and O-alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyryils. Synthesis of isoxazolo[5,4-f]- and pyrazolo[3,4-f]quinolines

  • A. K. Shanazarov
  • V. A. Kuzovkin
  • V. V. Chistyakov
  • V. G. Granik
Article
  • 146 Downloads

Abstract

The alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyrils has been examined by GLC. It has been found that, irrespective of the reaction conditions and the alkylating agent used, both N- and O-alkylation occur. When triethyloxonium fluoroborate and N,N-DMF diethyl acetal are used O-alkylation predominates, and with alkyl halides, N-alkylation. Reaction of N-ethyl-5-oxo-5,6,7,8-tetrahydrocarbostyril and 2-ethoxy-5-oxo-5,6,7,8-tetrahydrotetrahydroquinoline with DMF diethyl acetal gives the 6-dimethylaminomethylene derivatives, treatment of which with hydrazine hydrate or hydroxylamine affording isoxazolo[5,4-f]- or pyrazolo[3,4-f]quinolines.

Keywords

Acetal Hydrate Amide Diethyl Hydrazine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • A. K. Shanazarov
    • 1
  • V. A. Kuzovkin
    • 1
  • V. V. Chistyakov
    • 1
  • V. G. Granik
    • 1
  1. 1.S. Ordzhonikidze All-Union Research Institute for Pharmaceutical ChemistryMoscow

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