- Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
-
The general synthesis of diversely substituted dibenzoxepinones by a combined Pd-catalyzed α-arylation and SNAr strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α-arylation reaction.
- Deichert, Julie A.,Mizufune, Hideya,Patel, Jignesh J.,Hurst, Timothy E.,Maheta, Ashish,Kitching, Matthew O.,Ross, Avena C.,Snieckus, Victor
-
supporting information
p. 4693 - 4697
(2020/05/08)
-
- Discovery of novel benzylidene-1,3-thiazolidine-2,4-diones as potent and selective inhibitors of the PIM-1, PIM-2, and PIM-3 protein kinases
-
Novel substituted benzylidene-1,3-thiazolidine-2,4-diones (TZDs) have been identified as potent and highly selective inhibitors of the PIM kinases. The synthesis and SAR of these compounds are described, along with X-ray crystallographic, anti-proliferati
- Dakin, Les A.,Block, Michael H.,Chen, Huawei,Code, Erin,Dowling, James E.,Feng, Xiaomei,Ferguson, Andrew D.,Green, Isabelle,Hird, Alexander W.,Howard, Tina,Keeton, Erika K.,Lamb, Michelle L.,Lyne, Paul D.,Pollard, Hannah,Read, Jon,Wu, Allan J.,Zhang, Tao,Zheng, Xiaolan
-
scheme or table
p. 4599 - 4604
(2012/08/07)
-
- Synthesis of [1]Benzothieno[3,2-d]pyrimidines Substituted with Electron Donating Substituents on the Benzene Ring
-
Various 2-fluorobenzonitriles were converted to the corresponding 3-amino[1]benzothiophenecarboxylic acid esters, which in turn were annulated with formamidine or various equivalents to produce the desired tricyclic benzothienopyrimidines. Various methoxy and nitro/amino substituants were placed on the phenyl ring, requiring several different strategies to prepare the desired benzothiophenes. Several different pyrimidone annulations were also required. The use of an electron rich 2-bromobenzonitrile in a four-step one-pot low temperature lithiation sequence to produce highly electron-rich amino[1]benzothiophenecarboxylate esters is also described. The synthesis of 7-amino-8-fluoro[1]benzothieno[3,2-d]pyrimid-4(3H)-one was relatively straightforward, but synthesis of the corresponding 7-amino-8-protio analogue proved to be very difficult, and required several approaches before a successful one was found.
- Bridges, Alexander J.,Zhou, Hairong
-
p. 1163 - 1172
(2007/10/03)
-
