Details
| Original language | English |
|---|---|
| Article number | st-2017-b0101-l |
| Pages (from-to) | 121-125 |
| Number of pages | 5 |
| Journal | Synlett |
| Volume | 29 |
| Issue number | 1 |
| Publication status | Published - 22 Aug 2017 |
Abstract
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex ® (celecoxib).
Keywords
- antiinflammation, heteroarenes, organocatalysis, Stetter reaction, trifluoromethyl group
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Synlett, Vol. 29, No. 1, st-2017-b0101-l, 22.08.2017, p. 121-125.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes
T2 - A Short Synthesis of Celebrex ® (Celecoxib)
AU - Sommer, Heiko
AU - Braun, Max
AU - Schröder, Benjamin
AU - Kirschning, Andreas
N1 - Funding information: The authors are indebted to Dr. R. D. Shannon of E. I. du Pont de Nemours and Co., U.S.A., who kindly furnished the electrolyte samples and thank the Consiglio Nazionale delle Ricerche for the financial support.
PY - 2017/8/22
Y1 - 2017/8/22
N2 - 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex ® (celecoxib).
AB - 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex ® (celecoxib).
KW - antiinflammation
KW - heteroarenes
KW - organocatalysis
KW - Stetter reaction
KW - trifluoromethyl group
UR - http://www.scopus.com/inward/record.url?scp=85028323009&partnerID=8YFLogxK
U2 - 10.1055/s-0036-1589097
DO - 10.1055/s-0036-1589097
M3 - Article
AN - SCOPUS:85028323009
VL - 29
SP - 121
EP - 125
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 1
M1 - st-2017-b0101-l
ER -