Abstract
A traceless solid-phase route to 1,4-disubstituted-6-nitro-3,4-dihydro-1H- quinazolin-2-ones is described. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl) propionic acid was tethered to Rink resin via its carboxylic group. The protected amine was coupled with an organic acid after Alloc-deprotection and the arylfluorine was displaced with a primary amine to generate a resin-bound aniline with two diversity points. The aniline was released via cleavage to produce the desired products in high yield and purity.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5361-5364 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 46 |
| Issue number | 32 |
| DOIs | |
| State | Published - Aug 8 2005 |
Keywords
- 3,4-Dihydro-1H-quinoline-2-one
- Solid-phase synthesis
- Traceless cleavage
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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Wang, X., Dixon, S., Kurth, M. J., & Lam, K. (2005). Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones. Tetrahedron Letters, 46(32), 5361-5364. https://doi.org/10.1016/j.tetlet.2005.06.012