- Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate
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The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.
- Fujitani, Tadahiro,Hong, Dachao,Ito, Satoru,Ji, Xinyi,Kon, Yoshihiro,Nakashima, Takuya,Osuga, Ryota,Sato, Kazuhiko,Yokoi, Toshiyuki
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- Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine
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A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.
- Ch Ghosh, Keshab,Banerjee, Isita,Sinha, Surajit
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supporting information
p. 2923 - 2934
(2018/12/04)
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- Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols
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An efficient synthesis of β-amino alcohols from a variety of epoxides and primary unbranched amines in the absence of any catalyst in high yields and regioselectivities is reported. A variety of polar mixed solvent systems allow for the selective formation of secondary amino alcohols over tertiary amino alcohols. The reaction scope extends to a wide variety of aromatic and aliphatic substituted epoxides and primary amines bearing complex functionality.
- Lizza, Joseph R.,Moura-Letts, Gustavo
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supporting information
p. 1231 - 1242
(2017/03/11)
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- Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates
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The synthesis of 2-(phenoxymethyl)oxirane derivatives from oxiran-2-ylmethyl benzenesulfonates was developed through a base promoted rearrangement. A new C-O bond was formed along with the unexpected cleavage of C-S bond via this process. This unusual reaction was characterized with mild reaction conditions, high efficiency, and excellent functional group tolerance. A plausible reaction mechanism was proposed on the basis of experimental results and control experiments.
- Shen, Chuang,Guo, Xiang,Yu, Jun,Zeng, Xian-Guo,Peng, Li,Zhao, Chuan-Meng,Zhang, Fu-Li
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supporting information
p. 273 - 278
(2017/02/10)
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- ANTI-INFECTIVE COMPOUNDS
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The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.
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Page/Page column 48; 49
(2015/02/25)
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- Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
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A short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution.
- Dias, Luiz Carlos,Farina, Lui Strambi,Ferreira, Marco Antonio Barbosa
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p. 184 - 190
(2013/05/08)
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- Novel Benzyl Sulfonamide Derivatives Useful As MOGAT-2 Inhibitors
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The present invention provides compounds of Formula below: and analogues thereof where the various substituent groups, R1, R2, R3, R4, R5 A, and X are described herein; or a pharmaceutical salt thereof; a method of treating a condition such as hypertrigly
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Paragraph 0057; 0058; 0059
(2013/08/14)
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- A new synthesis of sultams from amino alcohols
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The base-mediated cyclization of N,O-dimesylate derivatives of cyclic and acyclic amino alcohols provides a simple access to five- and six-member sultams: isothiazolidine-1,1-dioxides and thiazinane-1,1-dioxides respectively.
- Lad, Nitin,Sharma, Rajiv,Marquez, Victor E.,Mascarenhas, Malcolm
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p. 6307 - 6309
(2013/11/06)
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- SUBSTITUTED DIHYDRO AND TETRAHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF
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The present invention relates to a series of substituted dihydro and tetrahydro oxazolopyrimidinones, specifically, to a series of 2-substituted-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-ones and 2-substituted-2,3,5,6-tetra-hydro-oxazolo[3,2-a]pyrimidin-7-ones of formula (I): Wherein p, n, X, Y, R1, R2, R3, R4, R5, R6, R7 and R8 are as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.
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Page/Page column 20
(2010/04/23)
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- Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization
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Resulting from a vHTS based on a pharmacophore alignment on known β3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human β3-AR agonist, yielding a lead compound with an excellent cellular activity of EC50 = 20 pM, selectivity over hβ1- and hβ2-adrenoceptors and a promising safety profile.
- Tasler, Stefan,Baumgartner, Roland,Ammendola, Astrid,Schachtner, Josef,Wieber, Tanja,Blisse, Marcus,Rath, Sandra,Zaja, Mirko,Klahn, Philipp,Quotschalla, Udo,Ney, Peter
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scheme or table
p. 6108 - 6115
(2010/11/19)
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- Ring-conformer effects of the cyclopropyl group: First use of trans-(2r,3r)-cyclopropanecarbaldehydes as electrophiles in diastereoselective baylisihillman reaction
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trans-(2R,3R)-Cyclopropanecarbaldehydes are used as novel electrophiles in the Baylis-Hillman reaction to afford adducts in good yields (75-85%) and diastereoselectivities (60-90%).
- Krishna, Palakodety Radha,Kishore,Reddy, P. Srinivas
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scheme or table
p. 2605 - 2608
(2010/03/03)
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- A novel and simple asymmetric synthesis of CMI-977 (LDP-977): A potent anti-asthmatic drug lead
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A practical gram scale asymmetric synthesis of CMI-977 is described. A tandem double elimination of an α-chlorooxirane and concomitant intramolecular nucleophilic substitution was used as the key step. Jacobsen hydrolytic kinetic resolution and Sharpless
- Gurjar, Mukund K.,Murugaiah,Radhakrishna,Ramana,Chorghade, Mukund S.
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p. 1363 - 1370
(2007/10/03)
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- NOVEL THIAZOLIDONE-2 DERIVATIVES, 4-DIKETONE SUBSTITUTED, METHOD FOR OBTAINING THEM AND PHARMACEUTICAL COMPOSITONS CONTAINING SAME
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The present invention relates to the field of chemistry and more particularly to that of therapeutic chemistry. The subject of the present invention is more precisely new 5-phenoxyalkyl-2,4-thiazolidinediones of general formula I: in which A represents a
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- Studies on new phosphodiesterase inhibitors. I. Synthesis of 1-(2,3-epoxypropoxy)-2(4)-fluorobenzenes and 1-(2-hydroxy-3-morpholinopropoxy and piperazino)fluorobenzene derivatives
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A series of 1-(2,3-epoxypropoxy)-2(4)-fluorobenzenes and their corresponding 1-(2-hydroxy-3-morpholino propoxy and piperazino)fluorobenzene derivatives (8a-f) were synthesised via a short synthetic route in good chemical yields and were evaluated for inot
- Baker,Byrne,Economides,Javed
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p. 1045 - 1048
(2007/10/02)
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- 1-aryl-4-piperazinylcyclohexanecarbonitriles, the preparation and use thereof
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Compounds of the formula STR1 where Ar, R1, R2, P and Q have the meanings indicated in the description, and the preparation thereof are described. The compounds have antihypoxic and antiischemic action and are suitable for treating acute and chronic degenerative processes of the CNS and other organs.
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- PROSTANOIDS. XIV. (+/-)-11-DEOXY-13,14-DIHYDRO-13-THIA-16-ARYLOXY-17,18,19,20-TETRANORPROSTAGLANDINS-E1 - NEW HYBRID PROSTAGLANDIN ANALOGS
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11-Deoxy-13,14-dihydro-13-thia-16-aryloxy-17,18,19,20-tetranorprostaglandin-E1 and their diastereomers were synthesized by the conjugate 1,4-addition of 2-hydroxy-3-aryloxypropanethiols to 2-(6-ethoxycarbonylhexyl)-2-cyclopenten-1-one.
- Tolstikov, G. A.,Miftakhov, M. S.,Danilova, N. A.,Shitikova, O. V.,Khalilov, L. M.,Panasenko, A. A.
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p. 1082 - 1089
(2007/10/02)
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- 13-Thia-prostaglandins
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This disclosure describes novel 13-thia prostanoic acids and derivatives thereof useful in causing prostaglandin-like biological responses.
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