- A Stepwise Annulation for the Transformation of Cyclic Ketones to Fused 6 and 7-Membered Cyclic Enimines and Enones
-
The efficient construction of functionalized polycyclic structures is an important objective in organic synthesis. Herein, we disclose a three-step “[2 + n]” annulation method for the transformation of cyclic ketones to fused enimines and enones. The method relies on the Suzuki coupling reaction and the amide reductive alkenylation reaction. A series of fused bicyclic (6/6, 6/7, 8/7) and tricyclic (6/6/6; 6/6/7, 6/5/7) ring systems bearing an α,β-enimine or an α,β-enone functionality have been synthetized in good overall yields.
- Wu, Dong-Ping,He, Qian,Chen, Dong-Huang,Ye, Jian-Liang,Huang, Pei-Qiang
-
-
Read Online
- A short and convenient preparation of (E)-3-(1-cyclohexenyl)-2- propenoic acid using a palladium(II) complex-catalyzed olefination
-
A convenient, three-step preparation of (E)-3-(1-cyclohexenyl)-2- propenoic acid (1) from cyclohexanone was developed, which exploited the palladium(II) complex-catalyzed olefination of the triflate 3 as a key step.
- Lai, Gaifa,McAllister, Timothy
-
-
Read Online
- 2,4,6-Tri-tert-butylpyrimidine (TTBP): A cost effective, readily available alternative to the hindered base 2,6-di-tert-butylpyridine and its 4-substituted derivatives in glycosylation and other reactions
-
It is reported that 2,4,6-tri-tert-butylpyrimidine (TTBP), a highly sterically hindered base available through an efficient, cost-effective one pot sequence, is a replacement for 2,6-di-tert-butylpyridine and its 4-substituted analogs in glycosylation rea
- Crich,Smith,Yao,Picione
-
-
Read Online
- Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes
-
The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.
- Bandini, Marco,Battaglioli, Simone,Liu, Yang,Lombardi, Lorenzo,Menichetti, Arianna,Montalti, Marco,Valenti, Giovanni
-
supporting information
p. 4441 - 4446
(2021/06/28)
-
- Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes
-
Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.
- Cho, Seoyoung,McLaren, E. J.,Wang, Qiu
-
supporting information
p. 26332 - 26336
(2021/11/10)
-
- Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds
-
Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.
- Pallesen, Jakob S.,Narayanan, Dilip,Tran, Kim T.,Solbak, Sara M. ?.,Marseglia, Giuseppe,S?rensen, Louis M. E.,H?j, Lars J.,Munafò, Federico,Carmona, Rosa M. C.,Garcia, Anthony D.,Desu, Haritha L.,Brambilla, Roberta,Johansen, Tommy N.,Popowicz, Grzegorz M.,Sattler, Michael,Gajhede, Michael,Bach, Anders
-
p. 4623 - 4661
(2021/05/07)
-
- Alkenylation and Arylation of Peptides via Ni-Catalyzed Reductive Coupling of α- C-Tosyl Peptides with Csp2Triflates/Halides
-
A Ni-catalyzed reductive cross-coupling between α-C-tosyl peptides and Csp2 triflates/halides has been developed. This protocol enables the formation of various unnatural di- and tripeptides containing vinyl and aryl side chains, and it expands the applications of Ni-catalyzed reductive cross-coupling in late-stage diversification of peptides.
- Chen, Yunrong,Gong, Hegui,Ma, Guobin,Qian, Qun,Song, Yanhong,Sun, Deli,Tao, Xianghua
-
supporting information
p. 7418 - 7422
(2021/10/12)
-
- Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones
-
This work describes an electrochemically promoted nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions. Excellent substrate tolerance and good chemical yields can be achieved by graphene/nickel foam electrodes in an undivided cell. Further study to gain mechanistic insight into this electrochemical cross-coupling has been carried out.
- Zhang, Feng,Wang, Yang,Wang, Yi,Pan, Yi
-
supporting information
p. 7524 - 7528
(2021/10/02)
-
- Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes
-
Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.
- Mahecha-Mahecha, Camilo,Lecornué, Frédéric,Akinari, Sumita,Charote, Thomas,Gamba-Sánchez, Diego,Ohwada, Tomohiko,Thibaudeau, Sébastien
-
supporting information
p. 6267 - 6271
(2020/09/02)
-
- Metal-Free 1,2,3-Triazole Synthesis in Deep Eutectic Solvents
-
The metal-free regioselective preparation of 1,5- and 1,4-disubstituted triazoles is reported through a cycloaddition-elimination sequence. Reactions were carried out in environmentally friendly deep eutectic solvent (DES) and pure products were isolated
- Díez-González, Silvia,Haselgrove, Samuel,Sebest, Filip,White, Andrew J. P.
-
supporting information
p. 605 - 609
(2020/04/08)
-
- Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions
-
An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access of dicarbonylated products from the corresponding ketones.
- Zhang, Shaoke,Neumann, Helfried,Beller, Matthias
-
supporting information
p. 3528 - 3532
(2019/05/24)
-
- Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties
-
Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clinical trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiological conditions, reducing the overall activity of the drug candidates. Herein, we report the preparation of cis-restrained carbocyclic analogs of CA-4. The compounds, which differ by the size and hybridization of the carbocyclic ring have been evaluated for their cytotoxic properties and their ability to inhibit tubulin polymerization. Biological data, supported by molecular docking studies, identified cyclobutenyl and cyclobutyl derivatives of the natural product as highly promising drug candidates.
- Nowikow, Christina,Fuerst, Rita,Kauderer, Maria,Dank, Christian,Schmid, Walther,Hajduch, Marian,Rehulka, Jiri,Gurska, Sona,Mokshyna, Olena,Polishchuk, Pavel,Zupkó, István,Dzubak, Petr,Rinner, Uwe
-
-
- Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines
-
This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.
- Wang, Hong-Fa,Wang, Shi-Yue,Qin, Tian-Zhu,Zi, Weiwei
-
supporting information
p. 17911 - 17914
(2018/11/23)
-
- Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling to Form Highly Substituted 1,3-Dienes
-
The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5′-bis(trifluoromethyl)-2,2′-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.
- Olivares, Astrid M.,Weix, Daniel J.
-
supporting information
p. 2446 - 2449
(2018/02/28)
-
- Spiro-compound, and preparation method and application thereof
-
The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, and discloses a spiro-compound as shown in the following general formula, and a preparation method and application thereof. A bioactivity screening result shows that the
- -
-
Paragraph 0081; 0082; 0083; 0084; 0085
(2017/02/17)
-
- Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones
-
We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr
- Su, Xiaolong,Huang, Honggui,Yuan, Yaofeng,Li, Yi
-
supporting information
p. 1338 - 1341
(2017/01/24)
-
- Generation of cycloalkynes through deprotonation of cyclic enol triflates with magnesium bisamides
-
Deprotonative generation of cyclohexynes, cycloheptynes, and cyclooctynes was achieved by controlling the reactivities of transient anionic species from the corresponding enol triflates with magnesium bis(2,2,6,6-tetramethylpiperidide) as a base. The star
- Hioki, Yuto,Okano, Kentaro,Mori, Atsunori
-
supporting information
p. 2614 - 2617
(2017/03/09)
-
- Catalytic Multisite-Selective Acetoxylation Reactions at sp2 vs sp3 C-H Bonds in Cyclic Olefins
-
The first Pd-catalyzed multisite-selective acetoxylation reactions are disclosed at an unactivated alkene sp2 C-H bond versus secondary allylic sp3 C-H bond in cyclic olefins via the modulation of directing groups. The different directing groups overcome the key challenge in differentiating C-H bonds and provide a new controlling approach for site-specific C-H activation. A wide variety of substrates are readily acetoxylated under operationally simple conditions. Mechanistic studies suggest that different Pd (IV) intermediates were involved in the multisite-selective acetoxylation reactions.
- Zang, Zhong-Lin,Zhao, Sheng,Karnakanti, Shuklachary,Liu, Cheng-Lin,Shao, Pan-Lin,He, Yun
-
supporting information
p. 5014 - 5017
(2016/10/14)
-
- Selenium-catalyzed oxidative c(sp2)-h amination of alkenes exemplified in the expedient synthesis of (Aza-)indoles
-
A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp2)-N bonds in high yields and with excellent functional group tolerance.
- Ortgies, Stefan,Breder, Alexander
-
supporting information
p. 2748 - 2751
(2015/06/16)
-
- Tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts
-
The present report describes an efficient and clean generation of sulfenate salts (R1SO-) by pyrolysis of readily available tert-butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium-catalyzed cross-coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple C-S bond-forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di-tert-butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2-) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.
- Gelat, Fabien,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Perrio, Stéphane
-
supporting information
p. 2011 - 2016
(2015/06/23)
-
- Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis
-
A continuous-flow, two-step procedure for the preparation of α-CF3-substituted carbonyl compounds has been developed. The carbonyl substrates were converted in situ into the corresponding silyl enol ethers, mixed with the CF3 radical source, and then irradiated with visible light using a flow reactor based on transparent tubing and a household compact fluorescent lamp. The continuous protocol uses Eosin Y as an inexpensive photoredox catalyst and requires only 20 min to complete the two reaction steps.
- Cantillo, David,De Frutos, Oscar,Rincon, Juan A,Mateos, Carlos,Kappe, C. Oliver
-
supporting information
p. 896 - 899
(2014/03/21)
-
- Ene-hydrazide from enol triflate for the regioselective Fischer indole synthesis
-
Ene-hydrazide prepared from enol triflate undergoes a Fischer indolization reaction to give the corresponding indole with complete regioselectivity. The starting enol triflate is readily accessed in regiochemically defined form from the ketone precursor via various well-established methods. This new protocol was successfully applied to the synthesis of desbromoarborescidine A, a natural β-carboline alkaloid, difficult to prepare with conventional Fischer indole synthesis.
- Lim, Byeong-Yun,Jung, Bo-Eun,Cho, Cheon-Gyu
-
supporting information
p. 4492 - 4495
(2015/01/09)
-
- Pd-catalyzed cross-coupling of polyfluoroarenes with cyclic vinyl triflates
-
An effective method for Pd-catalyzed cross-coupling between polyfluoroarenes and cyclic vinyl triflates has been developed. This protocol provides a useful and facile access to polyfluoroarylated cyclic alkenes that are difficult to prepare otherwise. The advantages of this method are its high efficiency and operational simplicity.
- Yu, Yanbo,Wang, Zhen,Zhang, Xingang
-
p. 276 - 281
(2014/03/21)
-
- Palladium-catalyzed decarboxylative vinylation of potassium nitrophenyl acetate: Application to the total synthesis of (±)-goniomitine
-
Merge and divert: The natural product (±)-goniomitine was synthesized by a method featuring two key steps: 1) fragment coupling to a functionalized cyclopentene by a novel palladium-catalyzed decarboxylative vinylation reaction and 2) an unprecedented one-pot integrated oxidation/reduction/cyclization (IORC) process to convert the substituted cyclopentene into the tetracyclic skeleton of goniomitine with high chemo-, regio-, and diastereoselectivity.
- Xu, Zhengren,Wang, Qian,Zhu, Jieping
-
supporting information
p. 3272 - 3276
(2013/04/10)
-
- INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES
-
The present invention relates to compounds of formula (1) as claimed in claim 1, their use in the treatment or the prevention of viral disorders, including HIV. (Formula I)
- -
-
Page/Page column 130
(2012/10/18)
-
- Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source
-
Rhodium(II) dicarboxylate complexes were discovered to catalyze the intramolecular amination of unactivated primary, secondary, or tertiary aliphatic C-H bonds using aryl azides as the N-atom precursor. While a strong electron-withdrawing group on the nitrogen atom is typically required to achieve this reaction, we found that both electron-rich and electron-poor aryl azides are efficient sources for the metal nitrene reactive intermediate.
- Nguyen, Quyen,Sun, Ke,Driver, Tom G.
-
supporting information; experimental part
p. 7262 - 7265
(2012/06/16)
-
- CF3 radicals from triflic anhydride and collidine: Their trapping by a trimethylsilylenolether
-
The interaction of triflic anhydride with s-collidine in the presence of the (trimethylsilyl)enolether of acetophenone led to duplication products the structure of which could only be explained by the formation of CF3 radicals.
- Rudler, Henri,Parlier, Andrée,Denneval, Charline,Herson, Patrick
-
scheme or table
p. 738 - 741
(2010/09/12)
-
- Diversity-oriented synthesis of enantiomerically pure steroidal tetracycles employing stille/diels-alder reaction sequences
-
Various steroid analogues were synthesized by Stille coupling of bicyclo[4.3.0]nonenylstannanes cis-/trans-8 and 14 with cyclohexenol triflates 17 and 18 and subsequent Diels-Alder reactions of the resulting dienes. The enantiomerically pure bicyclo[4.3.0
- Suì?nnemann, Hans Wolf,Banwell, Martin G.,De Meijere, Armin
-
body text
p. 7236 - 7249
(2009/08/07)
-
- Aryl annulation of cyclic ketones via a magnesium carbometalation-6-π- electrocyclization protocol
-
(Chemical Equation Presented) A new strategy for the aryl annulation of cyclic ketones is described. Palladium(0) coupling of a propargyl alcohol with the enol triflate of a ketone and addition of vinylmagnesium chloride generates a triene as a magnesium
- Tessier, Pierre E.,Nguyen, Natalie,Clay, Matthew D.,Fallis, Alex G.
-
p. 767 - 770
(2007/10/03)
-
- COMPOUNDS WITH ACTIVITY AT ESTROGEN RECEPTORS
-
Disclosed herein are novel di-phenyl compounds and methods for using various di-phenyl compounds for treatment and prevention of diseases and disorders related to estrogen receptors.
- -
-
Page/Page column 45
(2010/02/14)
-
- Concave reagents, 45.1 2,6-Di-tert-butylpyridine-loaded dendrimers and their use in vinyl triflate synthesis
-
2,6-Di-tert-butyl-pyridine (DTBP) has been connected with dendrons and dendrimers of the Frechet type. Four dendrimers, both first and second generation derivatives have been synthesized and used as non-nucleophilic, recyclable bases in the formation of cyclohexenyl-1-triflate from cyclohexanone. Georg Thieme Verlag Stuttgart.
- Luening, Ulrich,Marquardt, Torsten
-
p. 1383 - 1388
(2007/10/03)
-
- Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes
-
Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.
- Scheiper, Bodo,Bonnekessel, Melanie,Krause, Helga,Fuerstner, Alois
-
p. 3943 - 3949
(2007/10/03)
-
- N-ARYLPHENYLACETAMIDE DERIVATIVES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
-
N-Arylphenylacetamide derivatives represented by the following formula [I]: (wherein R1 is C1-6 alkoxy, etc.; R2 is hydrogen, -(CH2)m-N(R6)(R7) (m is an integer of from 1 to 4; R
- -
-
-
- New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction
-
The Pd-catalyzed coupling reaction of lactam or lactone-derived vinyl triflates and phosphates with α-alkoxydienylboronates gives conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety. If subjected to mild acidic hydrolysis, these compounds undergo a 4π electrocyclization process (Nazarov reaction) which furnishes cyclopenta-fused O- and N-heterocycles in good yields. The scope of the work has been that of closely examining the role and effect of both the heteroatom and the heterocycle ring size on the outcome of the electrocyclization, as well as the torquoselectivity of this process. The presence of the heteroatom was essential in stabilizing the oxyallyl cation intermediate, thus allowing the reaction to occur. The ring size was also a basic parameter in the cyclization step: five-membered azacycles required more drastic conditions to give 5-5 fused systems and did so only after an initial hydrolysis to the corresponding divinyl ketones. As for the torquoselectivity, with both 2-methyl and 4-methyl substituted lactam derivatives steric interactions seem to have a role in forcing the conrotatory process to take place in one sense only: allowing the synthesis of diastereomerically pure compounds to be realized. Because different patterns of substitution on the heterocycle are compatible with the reaction conditions, the methodology developed could be very useful for the synthesis of natural products and biologically active compounds containing cyclopenta-fused O- and N-heterocycle moieties.
- Occhiato, Ernesto G.,Prandi, Cristina,Ferrali, Alessandro,Guarna, Antonio,Venturello, Paolo
-
p. 9728 - 9741
(2007/10/03)
-
- Prostaglandin endoperoxide H synthase biosynthesis inhibitors
-
The present invention describes pyridazinone compounds of formula I which are cyclooxygenase (COX) inhibitors, and in particular, are selective inhibitors of cyclooxygenase-2 (COX-2). COX-2 is the inducible isoform associated with inflammation, as opposed to the constitutive isoform, cyclooxygenase-1 (COX-1) which is an important “housekeeping” enzyme in many tissues, including the gastrointestinal (GI) tract and the kidneys. The selectivity of these compounds for COX-2 minimizes the unwanted GI and renal side-effects seen with currently marketed non-steroidal anti-inflammatory drugs (NSAIDs).
- -
-
-
- A soluble polymer-supported triflating reagent: a high-throughput synthetic approach to aryl and enol triflates.
-
[reaction: see text] The high-yielding synthesis and application of the first example of a polymer-supported reagent for the preparation of trifluoromethanesulfonates (triflates) is described. This new reagent efficiently triflates aryl alcohols and lithi
- Wentworth,Wentworth Jr.,Mansoor,Janda
-
p. 477 - 480
(2007/10/03)
-
- New electrochemical carboxylation of vinyl triflates. Synthesis of β-keto carboxylic acids
-
Electrochemical reduction of alicyclic vinyl triflates (1a-1e) in a DMF solution containing 0.1 M Bu4NBF4 under an atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode resulted in the cleavage of an ox
- Kamekawa, Hisato,Senboku, Hisanori,Tokuda, Masao
-
p. 1591 - 1594
(2007/10/03)
-
- Synthesis of complex ethynyladenosines using organic triflic enolates in palladium-atalyzed reactions: Potential agonists for the adenosine A2 receptor
-
Many high affinity adenosine A2 receptor agonists contain substituents at position 2 of the purine base. In the search for new methodology to develop C-2 substituted adenosine analogues, we have applied organic triflates in palladium-catalyzed cross-couplings that resulted in new 2-cycloalkylated ethynyl-adenosines. The organic triflates are derived from commercially available ketones and, when used in the crosscouplings, result generally in clean reactions with good yields. These are the first examples of the utilization of organic triflates in palladium-catalyzed cross-coupling reactions in the synthesis of modified nucleosides.
- Adah, Steven A.,Nair, Vasu
-
p. 6747 - 6754
(2007/10/03)
-
- A New and Convenient Synthesis of Alkyl and Aryl Pyrimidines
-
Vinyl triflates 1, which are obtained easily from the corresponding ketones, react in an excess of pure nitrile (80 deg C/20 hours) to form tri- and tetra-substituted alkyl and arylpyrimidines 4 and 5 in good yields (45-87percent).An isomeric mixture of p
- Martinez, A. Garcia,Herrera, A.,Martinez, R.,Teso, E.,Garcia, A.,et al.
-
p. 1237 - 1241
(2007/10/02)
-
- 4-(LITHIOMETHYL)-2,6-DI-T-BUTYLPYRIDINE: A USEFUL PRECURSOR FOR THE SYNTHESIS OF BIS(2,6-DI-T-BUTYL)PYRIDYL COMPOUNDS.
-
Reaction of 4-(lithiomethyl)-2,6-di-t-butylpyridine (2) with one-half equiv of I2 produces 1,2-bis(2,6-di-t-butylpyridyl)ethane (3) in 88percent isolated yield.Treatment of 2 with 1,2-bis(chloromethyl)benzene affords the new compound 1,2-bis2-(2,6-di-t-b
- Wright, Michael E.,Yamada, LoRee Y.
-
p. 1449 - 1452
(2007/10/02)
-
- HYDROGENOLYSIS OF ENOL TRIFLATES; A NEW METHOD FOR THE REDUCTION OF KETONES TO METHYLENE COMPOUNDS.
-
Hydrogenolysis of enol trifluoromethanesulphonates (enol triflates) gives the hydrocarbon in high yield; ketones can thus be converted to the corresponding methylene compounds in a two-step process under mild conditions.
- Jigajinni, Veerappa B.,Wightman, Richard H.
-
p. 117 - 120
(2007/10/02)
-