Synthesis and antitubercular activity of spiroheterocycles: 2,2 ',4 ',5 '-tetra-substituted-1,2,2 ', 4 '-tetrahydro-4H-spiro[isoquinoline-3,3 '-pyrazol]-4-ones

Ben Hadda T., Rahima B., Kerbal A., Baba B. F. , AKKURT M. , Demailly G., ...More

ARKIVOC, pp.276-288, 2007 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume:
  • Publication Date: 2007
  • Doi Number: 10.3998/ark.5550190.0008.e26
  • Title of Journal : ARKIVOC
  • Page Numbers: pp.276-288


Synthesis of a series of fourteen novel 2,2',4',5'-tetra-substituted-1,2,2',4'-tetrahydro-4H-spiro[isoquinoline-3,3'-pyrazol]-4-ones was accomplished in good yield by regio and steroselective 1,3-dipolar cycloaddition of alpha-chloro-aryliden-phenylhydrazones with (3Z)-3(arylidene)-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ones 4-8 with dipolarophiles [(3Z)-2-phenyl-3-(p-R-1-phenyl)-2,3-dihydroisoquinolin-4(1H)-ones] 1-3. The structure of the isolated products 9-22 was established through different spectroscopic techniques. X-ray crystal structure analysis of one of the products confirms the structure and the selective region and stereochemistry of this cycloaddition. Their antitubercular activity is evaluated.