84099-58-1Relevant academic research and scientific papers
BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS
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Page/Page column 334; 335, (2018/03/25)
Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.
Selective Base-free Transfer Hydrogenation of α,β-Unsaturated Carbonyl Compounds using iPrOH or EtOH as Hydrogen Source
Farrar-Tobar, Ronald A.,Wei, Zhihong,Jiao, Haijun,Hinze, Sandra,de Vries, Johannes G.
supporting information, p. 2725 - 2734 (2018/02/28)
Commercially available Ru-MACHOTM-BH is an active catalyst for the hydrogenation of several functional groups and for the dehydrogenation of alcohols. Herein, we report on the new application of this catalyst to the base-free transfer hydrogenation of carbonyl compounds. Ru-MACHOTM-BH proved to be highly active and selective in this transformation, even with α,β-unsaturated carbonyl compounds as substrates. The corresponding aliphatic, aromatic and allylic alcohols were obtained in excellent yields with catalyst loadings as low as 0.1–0.5 mol % at mild temperatures after very short reaction times. This protocol tolerates iPrOH and EtOH as hydrogen sources. Additionally, scale up to multi-gram amounts was performed without any loss of activity or selectivity. An outer-sphere mechanism has been proposed and the computed kinetics and thermodynamics of crotonaldehyde and 1-phenyl-but-2-en-one are in perfect agreement with the experiment.
SELECTIVE REDUCTION OF ALDEHYDES AND KETONES
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Page/Page column 47; 48; 49, (2017/12/01)
The present invention relates to a selective reduction of specific aldehydes and ketones to their corresponding alcohols.
Selective Hydrogenation of α,β-Unsaturated Aldehydes and Ketones by Air-Stable Ruthenium NNS Complexes
Puylaert, Pim,van Heck, Richard,Fan, Yuting,Spannenberg, Anke,Baumann, Wolfgang,Beller, Matthias,Medlock, Jonathan,Bonrath, Werner,Lefort, Laurent,Hinze, Sandra,de Vries, Johannes G.
, p. 8473 - 8481 (2017/06/28)
The selective hydrogenation of the carbonyl functionality of α,β-unsaturated aldehydes and ketones is catalysed by ruthenium dichloride complexes bearing a tridentate NNS ligand as well as triphenylphosphine. The tridentate ligand backbone is flexible, as evidenced by the equilibrium observed in solution between the cis- and trans-isomers of the dichloride precatalysts, as well as crystal structures of several of these complexes. The complexes are activated by base in the presence of hydrogen and readily hydrogenate carbonyl functionalities under mild conditions. Despite the activation by base, side reactions are negligible, even for aldehyde substrates, because of the low amount of base. Thus, the corresponding allylic alcohols can be isolated in very good yields on a 10–25 mmol scale. Turnover numbers up to 200 000 were achieved.
Selective hydrogenation of unsaturated carbonyls by Ni-Fe-based alloy catalysts
Putro, Wahyu S.,Kojima, Takashi,Hara, Takayoshi,Ichikuni, Nobuyuki,Shimazu, Shogo
, p. 3637 - 3646 (2017/08/21)
Ni-Fe alloy catalysts prepared by a simple hydrothermal method and subsequent H2 treatment exhibited the greatest activity and selectivity for the hydrogenation of biomass-derived furfural to furfuryl alcohol among the examined second metals, such as Al, Ga, In, Co, and Ti. This work reveals that the alloying of Ni and Fe is a key factor in achieving highly selective hydrogenation of the CO moiety in unsaturated carbonyl substrates. We found that decreasing the temperature of H2 treatment (i.e. decreasing the crystallite size), e.g. Ni-Fe(2)HT-573 K (TOF = 952 h-1), increased the activity compared to that over Ni-Fe(2)HT-673 (TOF = 375 h-1) for furfural hydrogenation. This result suggests that a low-coordinated Ni-Fe alloy was imperative for the catalytic cycle. Moreover, the effect of the metal/support interface was critical; despite the high catalytic performance of Ni-Fe/TiO2, Ni-Fe/Al2O3, and Ni-Fe/CeO2, Ni-Fe supported on SiO2, taeniolite, and hydrotalcite catalysts were ineffective. Vibrational studies using FT-IR measurement confirmed that furfural was physically adsorbed on the surface of the Ni-Fe alloy catalyst via an η1(O) configuration. The synthetic scope of the Ni-Fe catalytic system was very broad; various types of unsaturated carbonyls, such as unsaturated aromatics, unconjugated aliphatics, and a large substituent, were selectively converted into the corresponding unsaturated alcohols.
Site- and stereoselectivity in the photochemical oxetane formation reaction (Paterno-Buechi reaction) of tetrahydrobenzofuranols with benzophenone: hydroxy-directed diastereoselectivity?
Yabuno, Youhei,Hiraga, Yoshikazu,Abe, Manabu
, p. 822 - 823 (2008/12/22)
The Paterno-Buechi reactions of tetrahydrobenzofuranols with benzophenone were investigated to reveal site- and stereo-selectivity in oxetane formation reactions. Both selectivities were found to be largely dependent on the reaction temperature. The trans selectivity increased with a decrease in temperature, and the more-substituted oxetanes were selectively formed at high temperature. Copyright
HETEROCYCLIC COMPOUND
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Page/Page column 63, (2010/11/29)
[Object] To provide a novel compound having an excellent immunosuppressive activity with low toxicity or a pharmacological salt thereof. [Means to achieve the object] A compound having general formula (I) shown below or a pharmacologically acceptable salt thereof, or a pharmacologically acceptable prodrug thereof [wherein A represents a carboxyl group, or the like, B represents a hydrogen atom, or the like, V represents a single bond, a methylene group, or the like, n represents an integer of from 0 to 2, W represents a 5- to 7-membered heterocyclic group, or the like, Z represents a group selected from Substituent group A, or the like, and Substituent group A represents the group consisting of a halogen atom, a C1-C6 alkyl group, a C3-C7 cycloalkyl group.
Fixation of natural furanoeremophilane by Diels-Alder reaction
Iida, Kazunori,Mitani, Makoto,Kuroda, Chiaki
body text, p. 966 - 971 (2009/06/05)
Diels-Alder reaction of furanoeremophilan-6β-ol (petasalbin) and its synthetic analogue, 4-hydroxy-4,5,6,7-tetra-hydrobenzofuran, was studied using TV-ethyl- and N-phenylmaleimides as the dienophiles, affording corresponding adducts as mixtures of stereoisomers. The adduct of petasalbin and maleimide was also obtained when the latter compound was added to a crude extracted solution of Petasites japonicus var. giganteus. By using this method, it was estimated that the contents of unstable furanoeremophilan-10β-ol in L. cymbulifera is more than 32% of the extract.
Compounds, Compositions and methods for insect control
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Page/Page column 14, (2008/06/13)
Rapidly acting compositions having vapor phase insecticidal activity comprise natural products or natural product-based materials. Further, these materials are non-petroleum based, are typically 100% biodegradable, and typically do not persist in the environment, unlike traditional pesticides. The compositions kill susceptible insects on contact in seconds, even the notoriously hardy peripleneta species. The compositions also kill insects behind cracks and crevices and when sprayed onto absorbent surfaces such as wood and plasterboard, where traditional contact insecticides work poorly or not at all. New methods of testing insecticides can be used to quantify these effects.
Construction of three types of fused isoindoles via furan-pyrrole ring exchange reaction
Lee, Mase,Moritomo, Hiroyuki,Kanematsu, Ken
, p. 8169 - 8180 (2007/10/03)
The new synthetic route of three types of fused isoindoles using furan- pyrrole ring exchange reaction as the main synthetic strategy is presented. Benzoisoindoles 17, 28 and 38 were synthesised from bicyclic furans 14, 25 and 35 respectively, which were trapped with dimethyl acetylenedicarboxylate.
