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Synthesis of a series of fourteen novel 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H- spiro(isoquinoline-3,5'-isoxazol)-4-ones was accomplished in good yield by regio and stereoselective 1,3-dipolar cycloaddition of p-R 2 -benzadoxime 4-8 with dipolarophiles (3Z)-3- ((4-substituted-phenyl)methylidene)-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ones 1-3. The structure of the isolated products 9-23 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 also evaluated.

arkivoc

Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H-spiro[isoquinoline-3,5'-isoxazol]-4-ones