Bacsa Ildikó, Szemerédi Dávid, Wölfling János, Schneider Gyula, Fekete Lilla, Mernyák Erzsébet
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Beilstein J Org Chem. 2018 May 4;14:998-1003. doi: 10.3762/bjoc.14.85. eCollection 2018.
A facile Pd-catalyzed C(sp)-N coupling to provide a range of 2- or 4-[(subst.)phenyl]amino-13α-estrone derivatives has been achieved under microwave irradiation. The reactions were mediated with the use of Pd(OAc) as a catalyst and KOBu as a base in the presence of X-Phos as a ligand. The desired products have been obtained in good to excellent yields. The nature and the position of the aniline substituent at the aromatic ring influenced the outcome of the couplings. 2-Amino-13α-estrone was also synthesized in a two-step protocol including an amination of 2-bromo-13α-estrone 3-benzyl ether with benzophenone imine and subsequent hydrogenolysis.
在微波辐射下，实现了一种简便的钯催化C(sp)-N偶联反应，可提供一系列2-或4-[(取代)苯基]氨基-13α-雌酮衍生物。反应以醋酸钯为催化剂、叔丁醇钾为碱，并在X-Phos作为配体的存在下进行。所需产物的产率良好至优异。芳环上苯胺取代基的性质和位置影响偶联反应的结果。2-氨基-13α-雌酮也通过两步法合成，包括2-溴-13α-雌酮3-苄基醚与二苯甲酮亚胺的胺化反应以及随后的氢解反应。
