Tetrahedron
Tetrahedron
5 years ago

3-Methyl-4-nitro-5-isatylidenyl-isoxazoles as 1,3-dipolarophiles for synthesis of polycyclic 3,3′-pyrrolidinyl-dispirooxindoles and their biological evaluation for anticancer activities

3-Methyl-4-nitro-5-isatylidenyl-isoxazoles as 1,3-dipolarophiles for synthesis of polycyclic 3,3′-pyrrolidinyl-dispirooxindoles and their biological evaluation for anticancer activities
Developed herein is a diversity-oriented one-pot multicomponent synthesis of polycyclic 3,3′- pyrrolidinyl-dispirooxindoles 3 via a multicomponent 1,3-dipolar cycloaddition event of 3-methyl-4-nitro-5-isatylidenyl-isoxazoles 2 with azomethine ylides (thermally generated in situ from isatins and proline or thioproline). Products bearing four consecutive stereocenters consist of two oxindole moieties and a polycyclic pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused in one ring structure were smoothly obtained in high yields (up to 85% yield) with good diastereoselectivity (up to >20:1). Valuable features of this method were application of 3-methyl-4-nitro-5-isatylidenyl-isoxazoles as 1,3-dipolarophiles and the design of new hybrid architectures for biological screenings through the adequate fusion of these sub-units of isoxazole and 3,3′-pyrrolidinyl-dispirooxindole, generating drug-like molecules.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017307354

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