Abstract
A novel application of the TMSN3 modified Ugi 4-component reaction is disclosed for the solution phase synthesis of fused azepine-tetrazole libraries. The reaction of a N-Boc-α-amino aldehyde, secondary amine, methyl isocyanoacetate and trimethylsilylazide in methanol, followed by acid treatment, proton scavenging and reflux affords bicyclic azepine-tetrazoles. This efficient protocol, producing products with three diversity points, can be used to generate arrays of biologically relevant small molecules for general and targeted screening.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3681-3684 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 43 |
| Issue number | 20 |
| DOIs | |
| State | Published - May 13 2002 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy. / Nixey, Thomas; Kelly, Michael; Semin, David; Hulme, Christopher.
In: Tetrahedron Letters, Vol. 43, No. 20, 13.05.2002, p. 3681-3684.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy
AU - Nixey, Thomas
AU - Kelly, Michael
AU - Semin, David
AU - Hulme, Christopher
PY - 2002/5/13
Y1 - 2002/5/13
N2 - A novel application of the TMSN3 modified Ugi 4-component reaction is disclosed for the solution phase synthesis of fused azepine-tetrazole libraries. The reaction of a N-Boc-α-amino aldehyde, secondary amine, methyl isocyanoacetate and trimethylsilylazide in methanol, followed by acid treatment, proton scavenging and reflux affords bicyclic azepine-tetrazoles. This efficient protocol, producing products with three diversity points, can be used to generate arrays of biologically relevant small molecules for general and targeted screening.
AB - A novel application of the TMSN3 modified Ugi 4-component reaction is disclosed for the solution phase synthesis of fused azepine-tetrazole libraries. The reaction of a N-Boc-α-amino aldehyde, secondary amine, methyl isocyanoacetate and trimethylsilylazide in methanol, followed by acid treatment, proton scavenging and reflux affords bicyclic azepine-tetrazoles. This efficient protocol, producing products with three diversity points, can be used to generate arrays of biologically relevant small molecules for general and targeted screening.
UR - http://www.scopus.com/inward/record.url?scp=0037071230&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037071230&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(02)00636-6
DO - 10.1016/S0040-4039(02)00636-6
M3 - Article
VL - 43
SP - 3681
EP - 3684
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 20
ER -