20416-16-4Relevant academic research and scientific papers
Expedient synthesis of a highly substituted tropolone via a 3-oxidopyrylium [5+2] cycloaddition reaction
Baldwin, Jack E.,Mayweg, Alexander V.W.,Pritchard, Gareth J.,Adlington, Robert M.
, p. 4543 - 4545 (2003)
An expedient ten-step synthesis of a substituted tropolone is described. The synthesis involves a 3-oxidopyrylium [5+2] cycloaddition reaction with acrylonitrile as the key step, affording a highly functionalized [3.2.1]-bicycle 10 as a single regioisomer. The nitrile substituent of the reduced cycloadduct 12 permits efficient ether-bridge cleavage and tropolone 15 is obtained after a final bis-oxidation procedure. The pyranulose acetate cycloaddition precursor was derived from 3-methyl-2-furoate.
Synthesis of a highly functionalized core of verrillin
Saitman, Alec,Theodorakis, Emmanuel A.
, p. 2410 - 2413 (2013)
An efficient stereoselective synthesis of furanoverrillin (5), a highly functionalized core of verrillin (1), is reported. The synthetic strategy is based on constructing bicyclic lactone 17 prior to the 10-membered ring macrocyclization. The effect of the C4 methyl group on the furan reactivity is also discussed.
The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation
De Pascalis, Lucrezia,Yau, Mei-Kwan,Svatunek, Dennis,Tan, Zhuoting,Tekkam, Srinivas,Houk,Finn
supporting information, p. 3751 - 3754 (2021/05/10)
Oxanorbornadienes (ONDs) undergo facile Michael addition with thiols and then fragment by a retro-Diels-Alder (rDA) reaction, a unique two-step sequence among electrophilic cleavable linkages. The rDA reaction rate was explored as a function of the furan
Effective and Selective Catalysts for Cinnamaldehyde Hydrogenation: Hydrophobic Hybrids of Metal–Organic Frameworks, Metal Nanoparticles, and Micro- and Mesoporous Polymers
Yuan, Kuo,Song, Tianqun,Wang, Dawei,Zhang, Xiaotao,Gao, Xiong,Zou, Ye,Dong, Huanli,Tang, Zhiyong,Hu, Wenping
supporting information, p. 5708 - 5713 (2018/03/27)
Metal–organic frameworks (MOFs) as selectivity regulators for catalytic reactions have attracted much attention, especially MOFs and metal nanoparticle (NP) shelled structures, e.g., MOFs@NPs@MOFs. Nevertheless, making hydrophilic MOF shells for gathering hydrophobic reactants is challenging. Described here is a new and viable approach employing conjugated micro- and mesoporous polymers with iron(III) porphyrin (FeP-CMPs) as a new shell to fabricate MIL-101@Pt@FeP-CMP. It is not only hydrophobic and porous for enriching reactants, but also possesses iron sites to activate C=O bonds, thereby regulating the selectivity for cinnamyl alcohol in the hydrogenation of cinnamaldehyde. Interestingly, MIL-101@Pt@FeP-CMPsponge can achieve a high turnover frequency (1516.1 h?1), with 97.3 % selectivity for cinnamyl alcohol at 97.6 % conversion.
Enantioconvergent Biocatalytic Redox Isomerization
Liu, Yu-Chang,Merten, Christian,Deska, Jan
supporting information, p. 12151 - 12156 (2018/09/11)
Alcohol dehydrogenases can act as powerful catalysts in the preparation of optically pure γ-hydroxy-δ-lactones by means of an enantioconvergent dynamic redox isomerization of readily available Achmatowicz-type pyranones. Imitating the traditionally metal-
Pd-catalyzed reaction of aryl halides and propargyl furylmethyl ethers: A novel pathway to functionalized dihydroisobenzofurans
Chen, Lingzhu,Shen, Ruwei,Wu, Luling,Huang, Xian
, p. 5954 - 5962 (2013/09/12)
An interesting sequential reaction involving Sonogashira coupling, propargyl-allenyl isomerization, intramolecular [4 + 2] cycloaddition, and bridged oxa-ring opening has been realized, providing a facile method for the synthesis of functionalized dihydroisobenzofurans from easily accessible starting materials with a decent diastereoselectivity.
Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates
Hashmi, A. Stephen K.,Ghanbari, Mohammad,Rudolph, Matthias,Rominger, Frank
supporting information; experimental part, p. 8113 - 8119 (2012/08/28)
A series of furan-yne systems was transformed into the corresponding tetrasubstituted annelated phenol derivatives that bear one bromo group. The two-step procedure consisted of a phenol synthesis and a subsequent electrophilic bromination with N-bromosuccinimide (NBS). The reactions can be performed in a one-pot procedure with the same precatalyst. The halogenation reaction is highly selective only in the presence of the gold catalyst. En-diyne substrates were also suitable starting materials; then the pentasubstituted aromatic core showed a completely different substitution pattern for the phenolic products. Furthermore, a one-pot protocol that consisted of a gold-catalyzed phenol synthesis, a gold-catalyzed halogenation reaction, and a palladium-catalyzed Suzuki coupling was established. The overall efficiency of this procedure was excellent and the substrate scope of the reaction was broad. Copyright
Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: Incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty
Basarab, Gregory S.,Hill, Pamela,Eyermann, Charles J.,Gowravaram, Madhu,Kaeck, Helena,Osimoni, Ekundayo
scheme or table, p. 5600 - 5607 (2012/09/22)
Structure-activity relationships are presented around a series of pyrazolopyrimidinediones that inhibit the growth of Helicobacter pylori by targeting glutamate racemase, an enzyme that provides d-glutamate for the construction of N-acetylglucosamine-N-acetylmuramic acid peptidoglycan subunits assimilated into the bacterial cell wall. Substituents on the inhibitor scaffold were varied to optimize target potency, antibacterial activity and in vivo pharmacokinetic stability. By incorporating an imidazole ring at the 7-position of scaffold, high target potency was achieved due to a hydrogen bonding network that occurs between the 3-position nitrogen atom, a bridging water molecule and the side chains Ser152 and Trp244 of the enzyme. The lipophilicity of the scaffold series proved important for expression of antibacterial activity. Clearances in vitro and in vivo were monitored to identify compounds with improved plasma stability. The basicity of the imidazole may contribute to increased aqueous solubility at lower pH allowing for improved oral bioavailability.
NEW AMINOTHIAZOLES AS FBPASE INHIBITORS FOR DIABETES
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, (2009/06/27)
Compounds of formula (I) as well as pharmaceutically acceptable salts and esters thereof, wherein R1 to R3 have the significance given in claim 1 and which can be used in the form of pharmaceutical compositions.
Practical, scalable, high-throughput approaches to η3- pyranyl and η3-pyridinyl organometallic enantiomeric scaffolds using the achmatowicz reaction
Coombs, Thomas C.,Lee IV, Maurice D.,Wong, Heilam,Armstrong, Matthew,Cheng, Bo,Chen, Wenyong,Moretto, Alessandro F.,Liebeskind, Lanny S.
, p. 882 - 888 (2008/09/18)
(Figure Presented) A unified strategy for the high-throughput synthesis of multigram quantities of the η3-oxopyranyl- and η3-oxopyridinylmolybdenum complexes TpMo(CO)2(η 3-oxopyranyl) and TpMo(CO)2(η3- oxopyridinyl) is described (Tp = hydridotrispyrazolylborato). The strategy uses the oxa- and aza-Achmatowicz reaction for the preparation of these organometallic enantiomeric scaffolds, in both racemic and high enantiopurity versions.
