100725-29-9Relevant articles and documents
One-Pot Assembly of Fused Heterocycles via Oxidative Palladium-Catalyzed Cyclization of Arylols and Iodoarenes
Hong, Fenglin,Chen, Yingwen,Lu, Beili,Cheng, Jiajia
, p. 353 - 357 (2016)
A one-pot, two-step cyclization reaction of iodoarenes with diversified arylols, including 4-hydroxyquinoline, quinolinone, 4-hydroxypyridine and phenol, has been developed. By using this palladium-catalyzed formal tandem O-arylation, dehydrogenative cross-coupling reaction, a variety of biologically significant fused benzo[4,5]furo heterocycles and dibenzofurans were quickly assembled in high yields with excellent regioselectivity. Notably, the efficient one-pot reaction led to the heterocycles via sequential oxidation, iodination, isomerization and cyclization steps without purification of any reaction intermediates.
Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed dehydrogenative C-H activation/annulation
Panda, Niranjan,Mattan, Irshad,Ojha, Subhadra,Purohit, Chandra Shekhar
supporting information, p. 7861 - 7870 (2018/11/21)
In this report, we have described a FeCl3-catalyzed process involving intramolecular annulation of o-phenoxy diarylacetylenes via hydroarylation to afford a series of biologically potent fused seven-membered (6-7-6) ring compounds under mild reaction conditions. This reaction was believed to proceed through Friedel-Crafts type sequential carbometallation followed by protonation to produce phenyldibenz[b,f]oxepines. This method was also extended to synthesize seven-membered rings that are fused with coumarins.
Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers
Chen, Huangguan,Han, Jianwei,Wang, Limin
supporting information, p. 12313 - 12317 (2018/09/10)
By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-l-thyronine (3-T1) derivative was synthesized by this aryl migration procedure.
One-pot syntheses of 2,6-diiododiaryl ethers from para-EWG-substituted phenols by diacetoxyiodobenzene
Zhou, De-Jun,Yin, Shu-Qiang,Fan, Yun-Chang,Wang, Qiang
, p. 5387 - 5394 (2016/06/01)
2,6-Diiododiaryl ethers are not only useful blocks to construct substituted diaryl ethers but are also characteristic drug precursors. In this research, a one-pot tandem oxidation of phenols substituted with electron-withdrawing group at the para position by excess diacetoxyiodobenzene is proven as a novel and efficient method for preparing 2,6-diiododiaryl ethers. Using this method, three new 2,6-diiododiaryl ethers, namely, methyl 3,5-diiodo-2-methoxy-4-phenoxybenzoate (2), methyl 3,5-diiodo-4-phenoxybenzoate (6), and 1-(2,6-diiodo-4-nitrophenoxy)benzene (7) were readily obtained from the corresponding phenols, and the yields were good.
Synthesis of Dibenzofurans via C-H Activation of o-Iodo Diaryl Ethers
Panda, Niranjan,Mattan, Irshad,Nayak, Dinesh Kumar
, p. 6590 - 6597 (2015/10/06)
An efficient method for the synthesis of dibenzofuran from o-iododiaryl ether using reusable Pd/C under ligand-free conditions has been developed. Synthesis of o-iododiaryl ether was achieved in one pot through sequential iodination and O-arylation of phenol under mild reaction conditions.
BENZAMIDE AND NICOTINAMIDE COMPOUNDS AND METHODS OF USING SAME
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Paragraph 0168, (2015/07/15)
The present disclosure provides benzamide and nicotinamide compounds and pharmaceutical uses of the compounds. The compounds can be used to treat, for example, cancers such hematopoietic cancers (e.g., leukemia). The preferred compounds of the invention c
Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
Liu, Zhijian,Larock, Richard C.
, p. 347 - 355 (2007/10/03)
An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps.
Structural studies on bioactive compounds. 32. Oxidation of tyrphostin protein tyrosine kinase inhibitors with hypervalent iodine reagents
Wells, Geoffrey,Seaton, Angela,Steven, Malcolm F. G.
, p. 1550 - 1562 (2007/10/03)
Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3-methoxy-1-(substituted- vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted- vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-α, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autophosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 μM tamoxifen, suggesting that this compound has estrogen agonist activity.
