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 |
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Keywords
- 3,4-Dihydro-1H-quinoline-2-one
- Solid-phase synthesis
- Traceless cleavage
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones. / Wang, Xiaobing; Dixon, Seth; Kurth, Mark J.; Lam, Kit.
In: Tetrahedron Letters, Vol. 46, No. 32, 08.08.2005, p. 5361-5364.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones
AU - Wang, Xiaobing
AU - Dixon, Seth
AU - Kurth, Mark J.
AU - Lam, Kit
PY - 2005/8/8
Y1 - 2005/8/8
N2 - 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.
AB - 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.
KW - 3,4-Dihydro-1H-quinoline-2-one
KW - Solid-phase synthesis
KW - Traceless cleavage
UR - http://www.scopus.com/inward/record.url?scp=21844455806&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=21844455806&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2005.06.012
DO - 10.1016/j.tetlet.2005.06.012
M3 - Article
AN - SCOPUS:21844455806
VL - 46
SP - 5361
EP - 5364
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 32
ER -