534595-85-2Relevant articles and documents
Asymmetric Reductive Amination/Ring-Closing Cascade: Direct Synthesis of Enantioenriched Biaryl-Bridged NH Lactams
Zhang, Yao,Liu, Yun-Qi,Hu, Le'An,Zhang, Xumu,Yin, Qin
supporting information, p. 6479 - 6483 (2020/09/02)
We report here a Ru-catalyzed enantioselective synthesis of biaryl-bridged NH lactams through asymmetric reductive amination and a spontaneous ring-closing cascade from keto esters and NH4OAc with H2 as reductant. The reaction features broad substrate generality and high enantioselectivities (up to >99percent ee). To showcase the practical utility, a highly enantioselective synthesis of 5-ethylindolobenzazepinone C, a promising antimitotic agent, has been rapidly completed. Furthermore, the amide group in the products enables versatile elaborations through directed C-H functionalization.
Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes
Faizi, Darius J.,Davis, Ashlee J.,Meany, Fiach B.,Blum, Suzanne A.
supporting information, p. 14286 - 14290 (2016/11/11)
The first ring-forming thioboration reaction of C?C π bonds is reported. This catalyst-free method proceeds in the presence of a commercially available external electrophilic boron source (B-chlorocatecholborane) in good to high yields. The method is scalable and tolerates a variety of functional groups that are intolerant of other major borylation methods. The resulting borylated benzothiophenes participate in a variety of in situ derivatization reactions, showcasing that these borylated intermediates do not need to be isolated prior to downstream functionalization. This methodology has been extended to the synthesis of borylated dihydrothiophenes. Mechanistic experiments suggest that the operative mechanistic pathway is through boron-induced activation of the alkyne followed by electrophilic cyclization, as opposed to S?B σ bond formation, providing a mechanistically distinct pathway to the thioboration of C?C π bonds.
Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma
Praveen, Chandrasekaran,Ayyanar, Asairajan,Perumal, Paramasivan Thirumalai
supporting information; experimental part, p. 4170 - 4173 (2011/08/06)
A highly regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones via gold(III) chloride catalyzed cycloisomerization of 3-ethynyl-indole-2-carboxylic acid was achieved in good to excellent yields. These compounds were screened for their in vitro cytotoxicity against human cervical (HeLa) cell lines. Out of ten compounds, three compounds (7d, 7e and 7j) showed comparable proliferation inhibitory activity against the standard drug cisplatin. Compound 7d was found to be the most efficacious with IC50 value of 0.22 μM.