1207-12-1Relevant academic research and scientific papers
An efficient synthesis of pure 4,6-dimethyldibenzothiophene
Meille, Valerie,Schulz, Emmanuelle,Lemaire, Marc,Faure, Rene,Vrinat, Michel
, p. 3953 - 3960 (1996)
The synthesis of substituted dibenzothiophenes in the 4 and/or 6 positions has been optimized and pure 4,6-dimethyldibenzothiophene has been prepared by a new selective method; X-ray analysis of this compound is described.
Rhodium-Catalyzed Sequential Dehydrogenation/Deoxygenation in One-Pot: Efficient Synthesis of Dibenzothiophene Derivatives from Diaryl Sulfoxides
Huang, Qiufeng,Fu, Shurong,Ke, Shaojia,Xiao, Hanbing,Zhang, Xiaofeng,Lin, Shen
, p. 6602 - 6605 (2015)
A novel strategy for the synthesis of dibenzothiophene derivatives is established through a one-pot intramolecular cross-dehydrogenative-coupling reaction of diaryl sulfoxides followed by deoxygenation with a Rh/Ag catalytic system. The yields obtained were good to excellent (up to 96 %), therefore making the described protocol an attractive option for building dibenzothiophene compounds. A novel strategy for the synthesis of dibenzothiophene derivatives was established through a one-pot intramolecular cross-dehydrogenative-coupling reaction of diaryl sulfoxides followed by deoxygenation with a Rh/Ag catalytic system.
Preparation of partially hydrogenated 4,6-dimethyldibenzothiophenes
Kukula, Pavel,Gramlich, Volker,Prins, Roel
, p. 1623 - 1640 (2006)
The synthesis of three key intermediates of the hydrogenation pathway in the hydrodesulfurization of 4,6-dimethyldibenzothiophene (4,6-DM-DBT; 1) is described. The hydrogenated derivatives 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene (=4,6-dimethyl-1,2,3,4-tetrahydrodibenzothiophene; 4,6-DM-TH-DBT; 2), 1,2,3,4,4a,9b-hexahydro-4,6-dimethyldibenzothiophene (=4,6-dimethyl-1,2,3,4,4a,9b-hexahydrodibenzothiophene; 4,6-DM-HH-DBT; 3), and dodecahydro-4,6-dimethyldibenzothiophene (=4,6-dimethylperhydrodibenzothiophene; 4,6-DM-PH-DBT; 4) were prepared by direct hydrogenation of 1. The reactions were carried out in continuous and batch reactors by using metal sulfide as well as noble-metal catalysts. The influence of the reaction conditions on the formation of the products and the distribution of their stereoisomers was studied in detail. The isomers of the main products were isolated and characterized by NMR, GC/MS/MS, and X-ray crystal-structure diffractometry.
Expeditious and efficient syntheses of pure 4-methyl and 4,6-disubstituted dibenzothiophenes
Kuehm-Caubere, Catherine,Adach-Becker, Sandrine,Fort, Yves,Caubere, Paul
, p. 9087 - 9092 (1996)
4-Lithio and 4,6-dilithiodibenzothiophenes were efficiently obtained by lithiation of dibenzothiophene with BuLi and BuLi-TMEDA, respectively. Very pure 4-methyl- and 4,6-dimethyldibenzothiophenes, substrates of great request in hydrosulfirization studies were easily prepared, on large scale and in excellent yields.
Hydrodesulfurization of 4,6-dimethyldibenzothiophene and its hydrogenated intermediates over bulk Ni2P
Yang, Lei,Li, Xiang,Wang, Anjie,Prins, Roel,Wang, Yao,Chen, Yongying,Duan, Xinping
, p. 144 - 152 (2014)
The hydrodesulfurization (HDS) of 4,6-dimethyldibenzothiophene (4,6-DMDBT) and its hydrogenated intermediates 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene (TH-4,6-DMDBT) and 1,2,3,4,4a,9b-hexahydro-4,6- dimethyldibenzothiophene (HH-4,6-DMDBT) over a bulk Ni2P catalyst was studied at 340 °C and 4.0 MPa in the presence and absence of piperidine. The rate constants of all steps in the network of the HDS of 4,6-DMDBT were measured. The HDS of 4,6-DMDBT occurred predominantly through the hydrogenation (HYD) pathway, and the HYD and direct desulfurization pathways were about equally inhibited by piperidine. Piperidine inhibited the desulfurization of TH-4,6-DMDBT and 4,6-DMDBT in the same way, but did not affect that of HH-4,6-DMDBT. In contrast to the HDS of TH-4,6-DMDBT over metal sulfide catalysts and to the HDS of TH-DBT, a fast dehydrogenation of TH-4,6-DMDBT to 4,6-DMDBT was observed. Besides 4,6-DMDBT, a small amount of the methyl-migration isomers was detected in the dehydrogenation product of TH-4,6-DMDBT, which is ascribed to the metallic character of Ni2P.
Facile Synthesis of Thienoacenes via Transition-Metal-Free Ladderization
Akhmetov, Vladimir,Amsharov, Konstantin Yu,Feofanov, Mikhail,Takayama, Ryo
, p. 14759 - 14766 (2021/11/12)
Herein, we report a facile transition-metal-free approach to sulfur-containing heteroacenes from fluorinated oligophenylenes. Unlike most existing methods, the presented approach is not restricted to simple dibenzothiophene derivatives and thus appears to
Hydrodesulfurization of dibenzothiophene, 4,6-dimethyldibenzothiophene, and their hydrogenated intermediates over bulk tungsten phosphide
Yang, Lei,Li, Xiang,Wang, Anjie,Prins, Roel,Chen, Yongying,Duan, Xinping
, p. 330 - 343 (2015/09/01)
The kinetics of the hydrodesulfurization (HDS) of dibenzothiophene (DBT), 4,6-dimethyldibenzothiophene (4,6-DMDBT), and their hydrogenated intermediates over bulk tungsten phosphide (WP) was studied. WP possessed high hydrogenation/dehydrogenation activity but was highly sensitive to piperidine inhibition. 4,6-DMDBT reacted faster than DBT, and both DBT and 4,6-DMDBT reacted mainly through the hydrogenation pathway. The methyl groups suppressed the direct desulfurization of 4,6-DMDBT but significantly promoted the hydrogenation of 4,6-DMDBT and the dehydrogenation of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene (TH-4,6-DMDBT) and 1,2,3,4,4a,9b-hexahydro-4,6-dimethyldibenzothiophene, but decreased the rate of hydrogenation of TH-4,6-DMDBT. Piperidine inhibited the HDS of 4,6-DMDBT much more strongly than that of DBT. Substantial dehydrogenation of TH-4,6-DMDBT to 4,6-DMDBT and two of its isomers occurred. The formation of these 4,6-DMDBT isomers in the dehydrogenation of TH-4,6-DMDBT and the hydrocracking of 1-methyl-4-(3-methylcyclohexyl)-benzene, as well as the formation of cyclopentylphenylmethane and (cyclopentylmethyl)cyclohexane, is ascribed to the metallic character of WP.
Synthesis of dibenzothiophenes by pd-catalyzed dual C-H activation from diaryl sulfides
Che, Rui,Wu, Zhiqing,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 7258 - 7261 (2014/06/23)
Palladium-catalyzed dual C-H functionalization of diaryl sulfides to form dibenzothiophenes (DBTs) by oxidative dehydrogenative cyclization is reported. This protocol afforded various DBTs in moderate to good yields with tolerance of a wide variety of substrates. Benzo[1,2-b:4,5-b]bis[b]benzothiophene was successfully synthesized by this method, which was used as an organic semiconductor for field-effect transistors.
Active-alkali metal promoted reductive desulfurization of dibenzothiophene and its hindered analogues
Pittalis, Mario,Azzena, Ugo,Pisano, Luisa
, p. 207 - 211 (2013/01/15)
Dibenzothiophene and some related organosulfur compounds are efficiently reductively desulfurized under mild reaction conditions, with Na and/or Li metal in the presence of a catalytic amount of tetraphenylethylene in THF at room temperature. This simple methodology was applied to the synthesis of several substituted biphenyls, thus realizing a connection between the directing properties of the sulfur atom of dibenzothiophene and the efficiency of 1,2-dianions of tetraphenylethane as homogenous electron transfer reagents.
Discovery of benzylisothioureas as potent divalent metal transporter 1 (DMT1) inhibitors
Zhang, Zaihui,Kodumuru, Vishnumurthy,Sviridov, Serguei,Liu, Shifeng,Chafeev, Mikhail,Chowdhury, Sultan,Chakka, Nagasree,Sun, Jianyu,Gauthier, Simon J.,Mattice, Maryanne,Ratkay, Laszlo G.,Kwan, Rainbow,Thompson, Jay,Cutts, Alison Brownlie,Fu, Jianmin,Kamboj, Rajender,Goldberg, Y. Paul,Cadieux, Jay A.
scheme or table, p. 5108 - 5113 (2012/08/28)
Inhibition of intestinal brush border DMT1 offers a novel therapeutic approach to the prevention and treatment of disorders of iron overload. Several series of diaryl and tricyclic benzylisothiourea compounds as novel and potent DMT1 inhibitors were discovered from the original hit compound 1. These compounds demonstrated in vitro potency against DMT1, desirable cell permeability properties and a dose-dependent inhibition of iron uptake in an acute rat model of iron hyperabsorption. Tricyclic compounds increased the in vitro potency by up to 16-fold versus the original hit. Diaryl compounds 6b and 14a demonstrated significant iron absorption inhibition in vivo with both 25 and 50 mg/kg doses. The diaryl and tricyclic compounds described in this report represent promising structural templates for further optimization.
