Back to Search
Start Over
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.
- Source :
-
Tetrahedron . Aug2017, Vol. 73 Issue 34, p5176-5188. 13p. - Publication Year :
- 2017
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 73
- Issue :
- 34
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 124320758
- Full Text :
- https://doi.org/10.1016/j.tet.2017.07.011