DOI: 10.3390/molecules29081790 ISSN: 1420-3049
Diastereoselective Three-Component 1,3-Dipolar Cycloaddition to Access Functionalized β-Tetrahydrocarboline- and Tetrahydroisoquinoline-Fused Spirooxindoles
Yongchao Wang, Yu Chen, Shengli Duan, Yiyang Cao, Wenjin Sun, Mei Zhang, Delin Zhao, Donghua Hu, Jianwei Dong- Chemistry (miscellaneous)
- Analytical Chemistry
- Organic Chemistry
- Physical and Theoretical Chemistry
- Molecular Medicine
- Drug Discovery
- Pharmaceutical Science
A chemselective catalyst-free three-component 1,3-dipolar cycloaddition has been described. The unique polycyclic THPI and THIQs were creatively employed as dipolarophiles, which led to the formation of functionalized β-tetrahydrocarboline- and tetrahydroisoquinoline-fused spirooxindoles in 60–94% of yields with excellent diastereoselectivities (10: 1−>99: 1 dr). This reaction not only realizes a concise THPI- or THIQs-based 1,3-dipolar cycloaddition, but also provides a practical strategy for the construction of two distinctive spirooxindole skeletons.