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) |
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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