476-34-6Relevant articles and documents
COS-triggered oxygen/sulfur exchange of isatins: Chemoselective synthesis of functionalized isoindigos and spirothiopyrans: Via self-condensation and the thio-Diels-Alder reaction
Chen, Wei,Lu, Xiao-Bing,Ren, Bai-Hao,Ren, Wei-Min,Zhou, Hui
supporting information, p. 678 - 685 (2022/02/01)
Herein, we present the first organocatalytic oxygen/sulfur atom exchange reaction (O/S ER) of isatins by employing carbonyl sulfide (COS) as a novel sulfuring reagent under mild reaction conditions. 8-Diazabicyclo[5.4.0]undec-7-ene (DBU) exhibited excellent activity in this approach. Remarkably, the chemical transformations of in situ generated 3-thioisatins can be tuned via the judicious choice of reaction solvents in a one pot process, enabling the selective formation of either functionalized isoindigos in CH3CN via a self-condensation process or spirothiopyrans in DMSO in the presence of conjugated dienes via the thio-Diels-Alder reaction. Mechanistic studies with experimental and density functional theory approaches revealed that the O/S ER between isatins and COS results in the formation of 3-thioisatins as the key intermediates, which further undergo solvent-controlled transformations to generate isoindigos or spirothiopyrans, respectively. The easily-accessible substrates and operational simplicity make the process suitable for further exploration. The practicality of this transformation was demonstrated by the gram-scale synthesis of isoindigo-based drug molecules and donor-acceptor conjugated polymers. This journal is
Perfluorobutyl substituted compound as well as preparation method and application thereof (by machine translation)
-
Paragraph 0112-0115, (2019/09/13)
The invention discloses a perfluorobutyl substituted compound as well as a preparation method and application; and a preparation method and application thereof. The chemical structural formula of the compound is as shown in formula (III), (VI), (X), wherein R is a branched alkane or a straight-chain alkane having 8~16 carbon atoms, and the compound has better dissolving performance, and the yield of each step is higher than the unitunityl ?. 10%. There is better air stability compared to compounds which are not substituted with fluoroalkyl groups, for example. The LUMO, HOMO energy level and the like are reduced, so that electron injection and transmission, and the maximum absorption wavelength in the field, of organic field effect transistors (OFET), organic solar cells (OPV), have potential application prospects. (by machine translation)
Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine
Chen, Si-Kai,Ma, Wen-Qiang,Yan, Zhi-Bo,Zhang, Fu-Min,Wang, Shao-Hua,Tu, Yong-Qiang,Zhang, Xiao-Ming,Tian, Jin-Miao
supporting information, p. 10099 - 10103 (2018/08/23)
A novel chiral spirocyclic amide (SPA)-derived triazolium organocatalyst has been designed and demonstrated to effect asymmetric homo- and heterodialkylations of various bisoxindoles, enabling enantioselective construction of vicinal all-carbon quaternary stereocenters. These reactions feature excellent enantio- and diastereoselectivities (up to 99% ee and >20:1 dr) as well as good to high yields (up to 89% over two steps). As an application of this methodology, the first asymmetric total synthesis of (-)-chimonanthidine has been achieved.