- Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals
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The intramolecular ionic Diels-Alder reaction of α-acetylenic acetals as a precursor of the propargyl cation has been investigated in the presence of Lewis acids and in protic acids. The reaction of diene-tethered α-acetylenic acetals (1-2) with formic acid yielded the regioselective intramolecular ionic Diels-Alder reaction products, bicyclodienal (9) and bicyclodienone (11) derivatives, in good yields.
- Shim, Seung-Bo,Ko, Yoon-Joo,Yoo, Byeong-Wook,Lim, Chang-Keun,Shin, Jung-Hyu
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- Intramolecular Cycloaddition Reactions of Conjugated Enynes
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The intramolecular cycloaddition of conjugated enynes provides an efficient and general route to aromatic and dihydroaromatic compounds.
- Danheiser, Rick L.,Gould, Alexandra E.,Pradilla, Roberto Fernandez de la,Helgason, Anna L.
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Read Online
- MODULATORS OF HSD17B13 AND METHODS OF USE THEREOF
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The disclosure relates to compounds and pharmaceutical compositions capable of modulating the hydroxysteroid 17-beta dehydrogenase (HSD17B) family member proteins including inhibiting the HSD17B member proteins, e.g. HSD17B13. The disclosure further relates to methods of treating liver diseases, disorders, or conditions with the compounds and pharmaceutical compositions disclosed herein, in which the HSD17B family member protein plays a role.
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Paragraph 0520
(2021/01/23)
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- Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light
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An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.
- Sherwood, Trevor C.,Xiao, Hai-Yun,Bhaskar, Roshan G.,Simmons, Eric M.,Zaretsky, Serge,Rauch, Martin P.,Knowles, Robert R.,Dhar, T. G. Murali
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p. 8360 - 8379
(2019/09/03)
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- Intramolecular Büchner reaction and oxidative aromatization with SeO2 or O2
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Intramolecular Büchner reaction of 1-diazo-5-phenylpentan-2-ones followed by oxidation with SeO2 or O2 in the presence of silica gel regioselectively gave 8-formyl-1-tetralones or one-carbon-lacking 1-tetralones, respectively.
- Morita, Shunya,Yoshimura, Tomoyuki,Matsuo, Jun-ichi
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p. 729 - 732
(2019/07/31)
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- Synthesis of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines
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By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.
- Chen, Hui,Zhao, Sihan,Cheng, Shaobing,Dai, Xingjie,Xu, Xiaoying,Yuan, Weicheng,Zhang, Xiaomei
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p. 1672 - 1683
(2019/04/08)
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- Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid
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Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.
- Zhang, Minmin,Yu, Shuowen,Hu, Fangzhi,Liao, Yijun,Liao, Lihua,Xu, Xiaoying,Yuan, Weicheng,Zhang, Xiaomei
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p. 8757 - 8760
(2016/07/15)
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- Method for synthesizing tetralone compound
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The invention belongs to the technical field of organic compound synthesis, provides a method for synthesizing a tetralone compound, and aims at solving the problems that in an exiting tetralone compound synthesizing method, an expensive transition metal catalyst, such as a palladium catalyst, is needed, and a large quantity of oxidizing agent is needed during a reaction. Aryl is used for replacing cyclobutanol to serve as an initiator, under the action of a catalyst, an oxidizing agent and an additive, reacting is carried out for 1-8 h in a solvent at the temperature of 25 DEG C to 100 DEG C, and the tetralone compound is obtained. The method has the advantages that the reaction conditions are relatively moderate, cheap metal copper is adopted as the catalyst, ligand participation is not needed, and operation is easy, convenient and feasible.
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Paragraph 0023; 0024
(2016/10/07)
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- A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion
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A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.
- Yu, Jiajia,Zhao, Huijun,Liang, Shuguang,Bao, Xiaoguang,Zhu, Chen
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supporting information
p. 7924 - 7927
(2015/07/27)
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- COMPOUNDS AND METHODS FOR TREATING HIV INFECTIONS
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The present invention is directed to novel nanomolar and picomolar inhibitors of HIV reverse transcriptase, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV-1 and HIV-2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.
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Paragraph 0449
(2015/04/21)
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- Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations
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The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.
- Romanov-Michailidis, Fedor,Romanova-Michaelides, Maria,Pupier, Marion,Alexakis, Alexandre
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p. 5561 - 5583
(2015/03/30)
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- Picomolar inhibitors of HIV-1 reverse transcriptase: Design and crystallography of naphthyl phenyl ethers
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Catechol diethers that incorporate a 6-cyano-1-naphthyl substituent have been explored as non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). Promising compounds are reported that show midpicomolar activity against the wild-type virus and sub-20 nM activity against viral variants bearing Tyr181Cys and Lys103Asn mutations in HIV-RT. An X-ray crystal structure at 2.49 ? resolution is also reported for the key compound 6e with HIV-RT.
- Lee, Won-Gil,Frey, Kathleen M.,Gallardo-Macias, Ricardo,Spasov, Krasimir A.,Bollini, Mariela,Anderson, Karen S.,Jorgensen, William L.
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supporting information
p. 1259 - 1262
(2015/04/27)
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- 4H-THIENO[3,2-C]CHROMENE-BASED INHIBITORS OF NOTUM PECTINACETYLESTERASE AND METHODS OF THEIR USE
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Compounds that may be used to inhibit Notum Pectinacetylesterase are described, as well as compositions comprising them, and methods of their use to treat diseases and disorders affecting bone.
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- 4,5-DIHYDRONAPHTHO [1,2-b] THIOPHENE DERIVATIVE
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A 4,5-dihydronaphtho[1,2-b]thiophene derivative expressed by the formula: (wherein R1 is a C1 to C10 1-hydroxyalkyl group or a C1 to C10 acyl group, and R2 and R3 separately substitute in the 6-, 7-, 8-, or 9-positions, and are each independently a hydrogen atom, a halogen atom, a C1 to C10 alkyl group, a hydroxy group, a C1 to C10 alkoxy group, a C1 to C5 alkenyloxy group, a C1 to C5 alkynyloxy group, a benzyloxy group, or the like, provided that when R1 is an acyl group and R2 is a hydrogen atom, then R3 is neither a hydrogen atom nor an acetyl group), or a pharmaceutically acceptable salt thereof. This is a novel compound that is effective in reducing triglyceride levels in the liver and reducing blood glucose levels.
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Page/Page column 15
(2010/11/08)
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- 4-Imidazole derivatives of benzyl and restricted benzyl sulfonamides, sulfamides, ureas, carbamates, and amides and their use
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Compounds of formula I are useful in treating diseases prevented by or ameliorated with α1A agonists. Also disclosed are α1A agonist compositions and a method of activating α1 adrenoceptors in a mammal.
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- Integrated chemical process: One-pot aromatization of cyclic enones by the double elimination methodology
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A variety of aromatic hydrocarbons bearing multiple alkyl substituents are accessible with perfect regiocontrol in a one-pot reaction starting from cyclo-hexenones and their aromatic analogues [Eq. (1)]. The present methodology can be further extended to the synthesis of polycyclic aromatic hydrocarbons. The drawbacks encountered in the Friedel-Crafts reaction are resolved since the reaction proceeds under basic conditions.
- Orita, Akihiro,Yaruva, Jayamma,Otera, Junzo
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p. 2267 - 2270
(2007/10/03)
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- A short, efficient synthesis of 6-cyano-1-tetralones
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A new, short and high-yield synthesis of 6-cyano-1-tetralones is described. Triflate intermediates 8 and 9 are versatile intermediates for the synthesis of other 6-substituted tetralones.
- Almansa,Carceller,Bartroli,Forn
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p. 2965 - 2971
(2007/10/02)
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- EFFECT OF THE 7-METHYL SUBSTITUENT ON THE RING OPENING PROCESS OF THE DIASTEREOISOMERIC BENZYLIC EPOXIDES DERIVED FROM 1,2,3,9,10,10a-HEXAHYDROPHENANTHRENE. DIFFERENCES AND SIMILARITIES BETWEEN DIFFERENT 2-ARYLOXIRANE MODELS
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The introduction of an electron-donating substituent (7-Me group) on the 1,2,3,9,10,10a-hexahydrophenanthrene system, influences differently the diastereoselectivity of the acid hydrolysis of the diastereoisomeric couples of benzylic epoxides 3a and 4a and 3b and 4b.While in 3b-4b an increase of the syn diastereoselectivity is observed, in 3a-4a a complete anti diastereoselectivity is found.On the other hand, the trichloroacetolyses of both 4a and 4b yield rearrangement products only, contrary to the unsubstituted derivatives 3a and 3b where consistent amounts of addition products were observed.The results obtained underline that system 3 presents apparent chemical similarities with system 2 and differs from 1 to which it is more closely related.
- Chini, Marco,Crotti, Paolo
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p. 733 - 739
(2007/10/02)
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- AROMATIC ANNULATION WITH BISPHENYLTHIONIUM IONS
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The chemospecific production and intramolecular aromatic electrophilic substitution (annulation) of bis(phenylthio)carbocations (bisphenylthionium ions) has been studied using appropriate model compounds.The annulation reaction is very sensitive to the Lewis acid initiator and also the solvent.The best reaction conditions were found to be a suspension of silver trifluoromethanesulfonate in dichloromethane.Annulation of six-membered rings onto alkylbenzene and five- and seven-membered rings onto activated benzenes have been achieved.
- Manas, Abdul Rahman Bin,Smith, Robin A. J.
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p. 1847 - 1856
(2007/10/02)
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- On structure of the adduct from the aluminium chloride catalyzed Diels-Alder reaction of 2-methyl-2-cyclohexenone with isopropene
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An unequivocal correlation of keto ester 3 and the adduct obtained from aluminium chloride catalyzed Diels-Alder reaction of 2-methyl-2-cyclohexenone with isoprene confirms the structure of the adduct to be 2.
- Das, Jagabandhu,Valenta, Zdenek,Liu, Hsing-Jang,Ngooi, Teng Ko
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p. 481 - 483
(2007/10/02)
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- 3-NITROCYCLOALKENONES, SYNTHESIS AND USE AS REVERSE AFFINITY CYCLOALKYNONE EQUIVALENTS
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A partical synthesis of 3-nitrocycloalkenones and their utilization as dienophiles in the Diels-Alder reaction are discribed.The results demonstrate a reverse affinity equivalency between these β-nitro-enones and "cycloalkynones".
- Corey, E. J.,Estreicher, Herbert
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p. 603 - 606
(2007/10/02)
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- Occupational medicine in Belgium
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In 1965 occupational medicine was extended to all Belgian industries. In view of the economical structure of the country, most of them became affiliated to occupational medical services. The supervision of workers' health and of the problems of industrial hygiene are the two main objectives of such a service.
- Brouwers
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p. 189 - 194
(2007/10/05)
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