123333-47-1Relevant academic research and scientific papers
2-Aryl-8-aza-3-deazaadenosine analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Nucleoside antibiotics that block siderophore biosynthesis in Mycobacterium tuberculosis
Krajczyk, Anna,Zeidler, Joanna,Januszczyk, Piotr,Dawadi, Surendra,Boshoff, Helena I.,Barry, Clifton E.,Ostrowski, Tomasz,Aldrich, Courtney C.
, p. 3133 - 3143 (2016)
A series of 5′-O-[N-(salicyl)sulfamoyl]-2-aryl-8-aza-3-deazaadenosines were designed to block mycobactin biosynthesis in Mycobacterium tuberculosis (Mtb) through inhibition of the essential adenylating enzyme MbtA. The synthesis of the 2-aryl-8-aza-3-deaz
1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane
Shibuya, Masatoshi,Matsuda, Miki,Yamamoto, Yoshihiko
, p. 8822 - 8831 (2021)
We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C?C bond formation with C?H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C?C bond with C?O bond scission at the silyloxy-substituted carbon.
Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives
Ichake, Sachin S.,Konala, Ashok,Kavala, Veerababurao,Kuo, Chun-Wei,Yao, Ching-Fa
, p. 54 - 57 (2017)
A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.
Perylene Bisimide and Naphthyl-Based Molecular Dyads: Hydrogen Bonds Driving Co-planarization and Anomalous Temperature-Response Fluorescence
Chou, Pi-Tai,Fang, Yu,Jiang, Qingwei,Liu, Fengyi,Liu, Ke,Shang, Congdi,Wang, Gang
, p. 8579 - 8585 (2020)
The origin of the positive temperature effect in fluorescence emission of a newly designed perylene bisimide (PBI) derivative with two naphthyl units containing ortho-methoxy group (NM) at its bay positions (PBI-2NM) was elucidated. A key point is the finding of a weak hydrogen bond (?1) between the methoxy group of the NM unit and a nearby hydrogen atom of the PBI core. It is the bonding that drives co-planarization of the different aromatic units, resulting in delocalization of the π-electrons of the compound as synthesized, inducing fluorescence quenching via intramolecular charge transfer (ICT). With increasing temperature, the co-planar structure could be distorted in part, resulting in a decreased degree of ICT, and hence leading to enhanced fluorescence emission. The unique positive temperature effect in emission induced by H-bond-driven co-planarization may pave a new avenue in designing functional molecular systems complementary to conventional methods.
Falling-solid flash vacuum pyrolysis: An efficient preparation of arylacetylenes
Wentrup, Curt,Becker, Jürgen,Winter, Hans-Wilhelm
, p. 5702 - 5704 (2015)
Automated falling-solid flash vacuum pyrolysis allows the rapid and efficient synthesis of a variety of arylacetylenes from 4-arylmethylidene-5(4H)-isoxazolone derivatives, which were prepared from aldehyde precursors. The acetylenes are readily obtained in multigram quantities. Taking the heat: Unlike in flash vacuum pyrolysis, involatile compounds can be used in falling-solid flash vacuum pyrolysis (FS-FVP). This method is employed for the rapid and efficient synthesis of a variety of arylacetylenes from 4-arylmethylidene-5(4H)-isoxazolones, which were in turn prepared from aldehyde precursors.
Supramolecular assemblies of chiral propargylic alcohols
Hyacinth, Marilise,Chruszcz, Maksymilian,Lee, Ki Sung,Sabat, Michal,Gao, Ge,Pu, Lin
, p. 5358 - 5360 (2006)
(Figure Presented) Six pack: A hexameric supramolecular structure with alternating enantiomers is formed in the solid state from propargylic alcohols. These hexamers further assemble to form channels and cages that host solvent molecules. The synergistic
Synthesis and properties of copper, mercury, and silver (2-naphthyl)acetylenides
Dikusar,Potkin,Vashkevich,Kozlov,Kaberdin
, p. 578 - 581 (2004)
(Z)-2-Naphthylacetylene was synthesized by the reaction of (Z)-3-(2-naphthyl)-3-chloropropenal (prepared from 2-acetylnaphthalene) with aqueous NaOH in dioxane. The reactions of 2-naphthylacetylene with CuCl, [Ag(NH3)2]NO3, and K2[HgI 4] gave copper, silver, and mercury 2-naphthylacetylenides, respectively. Silver naphthylacetylenide reacts with iodine to give the iodoethynyl derivative, which readily takes up bromine across the triple bond.
Compartmentalized host spaces accommodating guest aromatic molecules in a chiral way in a helix-peptide-aromatic framework
Uji, Hirotaka,Ogawa, Junya,Itabashi, Kenji,Imai, Tomoya,Kimura, Shunsaku
, p. 12483 - 12486 (2018)
A novel host molecular assembly of a free-standing flat nanosheet with compartmentalized spaces was prepared using a bolaamphiphilic peptide composed of two amphiphilic helical peptides and an oligo(naphthaleneethynylene) (ONE) unit at the center of the m
Sodium sulfide in methanol: A two-in-one reagent for deprotection of silyl and formation of propargyl sulfide
Hatial, Ishita,Mukherjee, Raja,Senapati, Kalyan,Basak, Amit
, p. 4275 - 4279 (2015)
A new reagent Na2S/MeOH for silyl deprotection has been developed. The reagent has several advantages which include deprotection of C-TMS, O-TMS, O-TBS, and O-TBDPS, selective removal of C-TMS and O-TMS in the presence of O-TBS and simultaneous
Segregated assemblies in bridged electron-rich and electron-poor π-conjugated moieties
Benanti, Travis L.,Saejueng, Pranorm,Venkataraman
, p. 692 - 694 (2007)
We report a general strategy for the spontaneous segregation of electron-rich and electron-poor π-conjugated moieties using mutually phobic aliphatic fluorocarbon-hydrocarbon interactions. The Royal Society of Chemistry.
