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4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes – a Short Synthesis of Celebrex® (Celecoxib)
Synlett ( IF 1.7 ) Pub Date : 2017-08-22 , DOI: 10.1055/s-0036-1589097 Andreas Kirschning 1 , Heiko Sommer 1 , Max Braun 2 , Benjamin Schröder 1
Synlett ( IF 1.7 ) Pub Date : 2017-08-22 , DOI: 10.1055/s-0036-1589097 Andreas Kirschning 1 , Heiko Sommer 1 , Max Braun 2 , Benjamin Schröder 1
Affiliation
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).
中文翻译:
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO),三氟甲基取代的杂芳烃的通用前体——Celebrex®(塞来昔布)的短合成
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) 作为一种含三氟甲基的结构单元,用于制备三氟甲基取代的噻吩、呋喃、吡咯和哌嗪。关键步骤是对 ETFBO 进行加成消除反应,然后是噻唑鎓催化的 Stetter 反应。这种化学的范围在针对 COX-2 选择性非甾体抗炎药 Celebrex®(塞来昔布)的新合成方法中得到证明。
更新日期:2017-08-22
中文翻译:
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO),三氟甲基取代的杂芳烃的通用前体——Celebrex®(塞来昔布)的短合成
4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) 作为一种含三氟甲基的结构单元,用于制备三氟甲基取代的噻吩、呋喃、吡咯和哌嗪。关键步骤是对 ETFBO 进行加成消除反应,然后是噻唑鎓催化的 Stetter 反应。这种化学的范围在针对 COX-2 选择性非甾体抗炎药 Celebrex®(塞来昔布)的新合成方法中得到证明。