- Reaction of tetramethylammonium fluoride with trifluoromethyltrimethylsilane
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Tetramethylammonium fluoride reacts with either triluoromethyltrimethylsilane or trimethylsilylacetonitrile in acetonitrile to form a pentacoordinate silicon species, which can act as a source of either fluoride or cyanomethyl carbanion, depending on substrate.
- Adams, Dave J.,Clark, James H.,Hansen, Liv B.,Sanders, Victoria C.,Tavener, Stewart J.
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Read Online
- AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles
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Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3-
- Gorbunova, Yelizaveta,Ryabukhin, Dmitry S.,Vasilyev, Aleksander V.
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p. 2663 - 2667
(2021/11/30)
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- Formation of Tetrahydrothiophenes via a Thia-Paternò-Büchi-Initiated Domino Photochemical Reaction
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We have established photochemical access to thietane or tetrahydrothiophene compounds from thiobenzophenone derivatives and acrylonitrile, wherein the product selectivity is controlled by a simple adjustment of the reagent concentration in solution. Small libraries of five-membered ring sulfur-containing compounds were prepared through a thia-Paternò-Büchi reaction, followed by a previously unknown regioselective photochemical ring enlargement reaction in a domino process or a stepwise fashion. A mechanism is proposed to rationalize this ring enlargement reaction via a carbene species provided from photoexcited thiocarbonyl compounds.
- Kassir, Ahmad F.,Guillot, Régis,Scherrmann, Marie-Christine,Boddaert, Thomas,Aitken, David J.
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p. 8522 - 8527
(2020/11/12)
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- Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy
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Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.
- Takahashi, Yoshiyuki,Tsuji, Hiroaki,Kawatsura, Motoi
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p. 2654 - 2665
(2020/02/04)
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- 5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations
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The synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.
- Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
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supporting information
p. 9496 - 9500
(2019/06/27)
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- Method of coupling, and the coupling method using the aromatic group-substituted heterocyclic compound
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Provided is an easy method (coupling method) capable of easily synthesizing a compound group in which aromatic molecules and aromatic molecules are coupled, a compound group in which aromatic molecules and alkene molecules are coupled, and the like without producing halogen waste and without the need to use scarce and expensive palladium. A compound (A) shown by general formula (A): Ar-H and a compound (B1) shown by general formula (B1): RaOCO-Ar', a compound (B2) shown by general formula (B2): RbCH=C(Ar")2, or a compound (B3) shown by general formula (B3): RcOCOCH=C(Ar")2 are reacted in the presence of a nickel compound.
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Paragraph 0234-0235; 0237
(2020/09/17)
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- Metal-Free Direct C?H Cyanation of Alkenes
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A metal-free and direct alkene C?H cyanation is described. Directing groups are not required and the mechanism involves electrophilic activation of the alkene by a cyano iodine(III) species generated in situ from a [bis(trifluoroacetoxy)iodo]arene and tri
- Wang, Xi,Studer, Armido
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supporting information
p. 11792 - 11796
(2018/09/10)
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- Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
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The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.
- Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Sharif, Muhammad,Kalevaru, Narayana V.,Jagadeesh, Rajenahally V.
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supporting information
p. 266 - 273
(2018/01/12)
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- Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles
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We have developed an easy and practical method for the synthesis of α,β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2OH·HCl) under metal-free conditions. By using or not using p-toluenesulfonyl chloride (p-TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step one-pot process in moderate to excellent yields with good functional group compatibility.
- Zhang, Qi,Zhang, Linjing,Tang, Chaojun,Luo, Huan,Cai, Xuediao,Chai, Yonghai
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supporting information
p. 6935 - 6942
(2016/10/14)
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- Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source
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The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and α,β-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.
- An, Xiao-De,Yu, Shouyun
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p. 5064 - 5067
(2015/11/03)
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- Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols with Hydroxylamine Hydrochloride to Give α,β-Unsaturated Amides and Alkenyl Nitriles
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We have developed a highly selective method for the synthesis of α,β-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH2OH·HCl) as the nitrogen source. The development of these new strategies has significantly extended the application of hydroxylamine hydrochloride to the chemistry of propargylic alcohols. Moreover, both secondary and tertiary alcohols have been highly regioselectively transformed to the desired products with good functional group compatibility.
- Han, Ya-Ping,Song, Xian-Rong,Qiu, Yi-Feng,Hao, Xin-Hua,Wang, Jia,Wu, Xin-Xing,Liu, Xue-Yuan,Liang, Yong-Min
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p. 9200 - 9207
(2015/09/28)
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- Bronsted acid mediated nitrogenation of propargylic alcohols: An efficient approach to alkenyl nitriles
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A novel and efficient approach to alkenyl nitriles from readily available propargylic alcohols has been developed. This nitrogenation reaction is transition-metal-free and could be conducted under air at ambient temperature, which makes this protocol promising and practical. Moreover, NH4Br is disclosed as an efficient additive to promote the stereoselectivity of this reaction. the Partner Organisations 2014.
- Huang, Xiaoqiang,Jiao, Ning
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supporting information
p. 4324 - 4328
(2014/06/23)
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- C-H alkenylation of azoles with enols and esters by nickel catalysis
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Rather u(Ni)que: Two new C-H alkenylation reactions, that is C-H/Ci£O alkenylation and decarbonylative C-H alkenylation, of azoles are uniquely catalyzed by Ni/dcype. These azole alkenylation reactions are successfully applied to the convergent formal synthesis of siphonazoleB.
- Meng, Lingkui,Kamada, Yuko,Muto, Kei,Yamaguchi, Junichiro,Itami, Kenichiro
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supporting information
p. 10048 - 10051
(2013/10/01)
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- Synthesis of acrylonitriles through an FeCl3-catalyzed domino propargylic substitution/aza-Meyer-Schuster rearrangement sequence
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Nontoxic cyanide source: An unprecedented route to acrylonitriles by employing propargylic alcohols and para-tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl3-catalyzed domino propargylic substitution/aza-Meyer-Schuster rearrangement sequence, the rearrangement process of which is reported for the first time. Copyright
- Hao, Lu,Wu, Feng,Ding, Zong-Cang,Xu, Su-Xia,Ma, Yan-Li,Chen, Li,Zhan, Zhuang-Ping
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supporting information; experimental part
p. 6453 - 6456
(2012/06/15)
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- Heck reactions catalyzed by Pd(0)-PVP nanoparticles under conventional and microwave heating
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Pd(0) nanoparticles stabilized by polyvinylpyrrolidone (Pd-PVP) with a diameter of 3-6 nm in ethanol catalyzed Heck coupling of iodobenzene with different alkenes under microwave heating. Products were obtained in good yields (62-99%) and good selectivity to the E-isomers. Microwave heating proved to be superior to conventional heating, providing products in higher yields and selectivities in short times (12 min).
- Martins, Daniela De L.,Alvarez, Heiddy M.,Aguiar, Lúcia C.S.,Antunes, Octavio A.C.
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experimental part
p. 47 - 53
(2012/04/11)
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- An efficient approach to alkenyl nitriles from allyl esters
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A novel and efficient approach to alkenyl nitriles from allyl esters has been developed. A tandem Pd-catalyzed substitution and the subsequent oxidative rearrangement are involved in this transformation. The method provides an important supplement for the synthesis of alkenyl nitriles from allyl esters. Georg Thieme Verlag Stuttgart · New York.
- Zhou, Wang,Xu, Jiaojiao,Zhang, Liangren,Jiao, Ning
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p. 887 - 890
(2011/06/17)
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- Iron-facilitated direct oxidative C-H transformation of allylarenes or alkenes to alkenyl nitriles
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This paper describes the first direct approach to alkenyl nitriles from allylarenes or alkenes facilitated by an inexpensive homogeneous iron catalyst. Three C-H bond cleavages occur under the mild conditions during this process. Mechanistic studies indic
- Qin, Chong,Jiao, Ning
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supporting information; experimental part
p. 15893 - 15895
(2011/01/03)
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- Direct oxidative coupling of benzenes with acrylonitriles to cinnamonitriles catalyzed by Pd(OAc)2/HPMoV/O2 system
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A facile direct synthesis of cinnamonitriles from acrylonitriles and benzenes is successfully achieved by using Pd(OAc)2/HPMoV/O 2 catalyst system via the direct C-H bond activation of benzenes using molecular oxygen as a terminal oxidant.
- Obora, Yasushi,Okabe, Yoshihisa,Ishii, Yasutaka
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supporting information; experimental part
p. 4071 - 4073
(2010/11/04)
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- DERIVATlVES OF UREA AND RELATED DIAMINES, METHODS FOR THEIR MANUFACTURE AND USES THEREFOR
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The present invention relates generally to compounds represented in Formula I, pharmaceutical compositions comprising them and methods of treating of diseases or disorders related to the function of the calcium sensing receptor. The invention also relates to processes for making such compounds and to intermediates useful in these processes
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Page/Page column 44
(2009/03/07)
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- Novel process for the synthesis of class I antiarrhythmic agent (±)-cibenzoline and its analogs
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Synthesis of (±)-cibenzoline and its analogs has been achieved by a simple sequence of reactions. The diaryl cyanoolefin intermediate 3 could be prepared by Knoevenagel condensation of benzophenone with ethylcyanoacetate to form the tetra-substituted olefin intermediate 2 followed by Krapcho deethoxycarbonylation or from β-hydroxynitrile intermediate 2' followed by the elimination of hydroxyl group respectively. The 2,2- diphenylcyclopropanecarbonitrile 4 was synthesized from intermediate 3 by cyclopropanation, which was converted to (±)-2-(2,2-diphenylcyclopropyl)- 2-imidazoline 5 by reaction with ethylenediamine in the presence of a catalytic amount of sulfur. Moreover, the obtained 2-imidazolines were smoothly oxidized to the corresponding imidazoles 6 in good to moderate yields. Copyright Taylor & Francis Group, LLC.
- Gholap, Atul R.,Paul, Vincent,Srinivasan, Kumar V.
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p. 2967 - 2982
(2008/12/22)
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- Phosphazene base-catalyzed condensation of trimethylsilylacetate with carbonyl compounds
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The t-Bu-P4 base was found to be an excellent catalyst for the condensation of trimethylsilylacetate or trimethylacetonitrile with carbonyl compounds to form functionalized alkenes and β-enaminoesters were also synthesized by the condensation with formanilides. The Royal Society of Chemistry 2006.
- Kobayashi, Koji,Ueno, Masahiro,Kondo, Yoshinori
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p. 3128 - 3130
(2008/09/20)
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- Mono- and β,β-double-heck reactions of α,β-unsaturated carbonyl compounds in aqueous media
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Optimized reaction conditions for the mono- and β,β-diarylation of electron-deficient alkenes in aqueous media catalyzed either by a p-hydroxyacetophenone oxime-derived palladacycle or by palladium(II) acetate under phosphine-free conditions and in the presence of (dicyclohexyl)- methylamine as base are described. Regioselective monoarylation of unsubstituted and substituted α,β-unsaturated carbonyl compounds takes place with aryl iodides at 120 °C in water. Aqueous N,N-dimethylacetamide (DMA), tetra-n-butylammonium bromide (TBAB) as additive, and the palladacycle as catalyst are the most efficient conditions for the coupling with aryl bromides, good stereoselectivities being also obtained in the arylation of crotonates and itaconates, whereas cinnamic derivatives afford lower steroselectivity, with the exception of cinnamic acid and nitrile. β,β-Diarylation of unsubstituted α,β-unsaturated carbonyl compounds can be controlled by using higher loading of the palladacycle and can be performed in refluxing water for aryl iodides, whereas DMA must be used for aryl bromides. Microwave irradiation can be used in the monoarylation of tertbutyl acrylate with aryl iodides in water or the coupling between ethyl cinnamate and aryl bromides in aqueous DMA.
- Botella, Luis,Najera, Carmen
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p. 4360 - 4369
(2007/10/03)
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- Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle
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The mono and β,β-diarylation of α,β-unsaturated carbonyl compounds with electron-deficient and electron-rich aromatic iodides in water is described. These reactions are catalyzed by the p- hydroxyacetophenone oxime-derived palladacycle 1 by controlling the stoichiometry of the aryl iodide and the alkene as well as the loading of the palladium catalyst. This one-pot protocol is performed in refluxing water and (dicyclohexyl)methylamine as base under thermal or microwave conditions and in the absence of an inert atmosphere.
- Botella, Luis,Nájera, Carmen
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p. 1833 - 1836
(2007/10/03)
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- Cascade Transformations of (2,2-Diaryl-3,3-dichloroaziridin-1-yl)acetates
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Esters of (2,2-diaryl-3,3-dichloroaziridin-1-yl)acetic acid prepared from glycine derivatives under alkylation conditions afford esters of 2-[N-alkyl-N-(2,2-diaryl-1-cyanovinyl)amino]-3,3-diarylacrylic acid in 20-40% yield. The reaction resulting in these compounds proceeds through a cascade of 3-chloro-2-azadiene and ylide intermediates. 3-Chloro-2-azadienes originating from (2,2-diaryl-3,3-dichloroaziridin-1-yl)-acetates react with primary and secondary amines at the carbon atom of imine group providing ketenimines which undergo ketenimine-nitrile rearrangement or fragmentation. The other bases (KOH, MeONa, DBU) effect dehydrochlorination of the mentioned 3-chloro-2-azadienes giving nitrile-ylides which are trapped by nucleophilic reagents. The 3-chloro-2-azadiene obtained from methyl (2,2-diaryl-3,3-dichloroaziridin-1-yl)- acetate and DBU was relatively stable and was isolated as an individual compound. (2,2-diaryl-3,3-dichloroaziridin-1-yl)propionates behave as nonfunctionalized dichloroaziridines.
- Khlebnikov,Novikov,Kusei,Kopf,Kostikov
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p. 559 - 573
(2007/10/03)
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- Experimental and theoretical studies on pyrolysis of O-acetyl derivatives of β-phenylcinnamaldehyde and benzaldehyde oximes
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Thermal behavior of β-phenylcinnamaldehyde and benzaldehyde oxime O-acetyl derivatives was studied experimentally and theoretically by the semi-empirical PM3 method. Intramolecular pericyclic mechanisms were proposed for the reactions of the E-isomers, intramolecular catalytic polar mechanism for elimination of acetic acid from the Z-isomers.
- Mohamed,Siedlecka,Suwinski
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p. 577 - 590
(2007/10/03)
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- Photochromic oxazine compounds and methods for their manufacture
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The present invention provides oxazine compounds having aromatic, heteroaromatic, or aliphatic substituents at the 2 position of the oxazine moiety. Additionally, a one pot method with excellent yields is provided for producing the compounds
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- Photochromic oxazine compounds and methods for their manufacture
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The present invention provides photochromic oxazine compounds and methods for their manufacture, which compounds are useful as photochromic compounds. The compounds of the invention have aromatic substituents on the 2 position of the oxazine moiety.
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- Stereospecific synthesis of 3,3-disubstituted acrylonitriles by Heck reaction
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The coupling reaction of 3-aryl (or heteroaryl) acrylonitriles with several aryl and heteroaryl iodides (Heck reaction) under Jeffery's conditions has been studied as a concept to synthesize, in a stereospecific manner, trisubstituted olefins.
- Masllorens, Judit,Moreno-Ma?as, Marcial,Pla-Quintana, Anna,Pleixats, Roser,Roglans, Anna
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p. 1903 - 1911
(2007/10/03)
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- New approaches towards the synthesis of alkenes using the Horner-Wadsworth-Emmons (HWE) reaction as the key step
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Leading from our work in asymmetric alkene synthesis it was discovered that the alkenylatio of aldehydes with phosphonates proceeds smoothly at room temperature in the absence of Lewis acidusing triethylamine as the base if the reaction is carried out at a pressure of 8 kbar. Based on this protoco a new domino process was developed, combining the HWE reaction with a Heck coupling, thus allowing the one pot synthesis of trisubstituted alkenes.
- Bodman, Kerstin,Has-Becker, Shenay,Reiser, Oliver
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p. 173 - 176
(2007/10/03)
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- Highly Efficient Pd-Catalyzed Coupling of Arenes with Olefins in the Presence of tert-Butyl Hydroperoxide as Oxidant
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(matrix presented) ArH : benznoid and non-benzenoid. R = H, CH3, Ph. R1 = Ph, CO2Et, COMe, CHO, CO2H, CN. The oxidative coupling of arenes with olefins has been performed efficiently in the presence of catalytic amounts of palladium acetate and benzoquinone (BQ) with tert-butyl hydroperoxide as the oxidant in up to 280 turnover numbers (TON). The catalytic system is especially active for the coupling of heterocycles such as furans and indole with activated olefins. The reaction is highly regio-and stereoselective, giving trans-olefins predominantly.
- Jia, Chengguo,Lu, Wenjun,Kitamura, Tsugio,Fujiwara, Yuzo
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p. 2097 - 2100
(2008/02/10)
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- Solvents as phase transfer catalysts. Reaction of trimethylsulfonium iodide and solid potassium hydroxide in acetonitrile leading to an epoxide of benzophenone
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The kinetics of reactions of benzophenone with trimethylsulfonium iodide in acetonitrile in the presence of excess solid potassium hydroxide (KOH) are reported, and the kinetics of formation of products, 2,2-diphenyloxirane, 2,2-diphenylacrylonitrile, and N-(2-hydroxy-2,2-diphenyl)acetainide are also monitored. The effects of water, other cosolvents and quaternary ammonium salts are investigated. Initial rates are lower than rates of comparable reactions involving nitrile formation in the absence of sulfonium salts, and the epoxide reaches a concentration maximum before any nitrile forms. The results can be explained by initial formation of the anion [CH2CN]-, which reacts with the sulfonium salt to give Me2S+CH2- (ylide, leading to epoxide) before direct reaction of [CH2CN]- with benzophenone (leading to nitrile) can occur. Consequently, acetonitrile is acting as a phase transfer catalyst, aiding the transport of base (in a modified form) from the surface of the KOH to form the ylide.
- Bentley, T. William,Jones, Ray V.H.,Larder, Annette H.,Lock, Stephen J.
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p. 1407 - 1411
(2007/10/03)
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- Role of water and phase transfer catalysts in the kinetics of condensation of diaryl ketones with acetonitrile initiated by solid potassium hydroxide
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The kinetics of reactions of benzophenone and substituted derivatives with acetonitrile in the presence of excess solid potassium hydroxide (KOH) to give 2,2-diarylacrylonitriles are reported. Reaction rates are strongly temperature dependent, and water,
- Bentley, T. William,Jones, Ray V. H.,Larder, Annette H.,Lock, Stephen J.
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- Stereospecific Preparation of (E) and (Z)-3,3-Diarylacrylonitriles by Heck Reaction
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Both isomers 5 and 8 of 3,3-diarylacrylonitrile constitution are obtained in highly diastereoselective Pd-catalyzed Heck reactions under Jeffery conditions between (E)-cinnamonitriles and aryl iodides.
- Moreno-Ma?as, Marcial,Pleixats, Roser,Roglans, Anna
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p. 1157 - 1158
(2007/10/03)
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- Stereoselective synthesis of 3-alkylcinnamonitriles
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Stereoselective synthesis of (2Z)-3-arylselenocinnamonitriles and coupling them with Grignard reagents catalysized by CuI, giving the trisubstituted alkenes with main retention products.
- Zhao, Chang-Qiu,Huang, Xian
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p. 3607 - 3611
(2007/10/03)
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- Reactivity of silylated compounds with active methylene under microwave irradiation in heterogeneous dry media; application to the alkali metal fluoride-mediated silyl-Reformatsky reaction
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The condensation of trimethylsilylacetic compounds 2a, 2b, (nitrile, ester) and trimethylsilylmethylphosphonic esters 2c with aromatic aldehydes 1, in the presence of alkali metal fluorides (potassium, cesium) unsupported or supported on alumina, magnesium oxide or clay (montmorillonite K10), is achieved by solvent-free techniques in a domestic microwave oven.The factors governing the reaction selectivity are studied.The silyl-Reformatsky reaction takes place in the presence of dried fluoride and leads to the silylated compound 3, which can be subsequently hydrolyzed to 4.The latter can be dehydrated to give the alkene 5.Keywords - alkali metal fluoride / silyl-Reformatsky reaction / nucleophilic activation / inorganic solid supports / trimethylsilyl-acetic compounds / microwave irradiation
- Latouche, R.,Texier-Boullet, F.,Hamelin, J.
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p. 535 - 546
(2007/10/02)
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- Hybrid Cholecystokinin-A Antagonists Based on Molecular Modelling of Lorglumide and L-364,718
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A series of novel nonpeptide cholecystokinin-A (CCK-A) antagonists have been synthesized.Designed on the basis of the structural homology between lorgumide and L-364,718, as investigated with molecular modeling, these compounds constitute a link between the N-acylglutamic acid and 3-amino-5-phenyl-1,4-benzodiazepin-2-one derived antagonists.The prepared compounds were tested in vitro as antagonists of the binding of -(+/-)-L-364,718 and -CCK-8(S) to rat pancreas and guinea pig brain membranes, respectively.All compounds proved to be selective for the(peripheral) CCK-A receptor, the most potent analogue, 6, having a Ki value of 90 nM.The structure-activity profile of the series of hybrid compounds relates closest to that of the N-acylglutamic acid derived antagonists.
- Bent, Arie van der,Blommaert, Armand G. S.,Melman, Caroline T. M.,IJzerman, Adriaan P.,Wijngaarden, Ineke van,Soudijn, Willem
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p. 1042 - 1049
(2007/10/02)
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- A highly active and stereoselective montmorillonite catalyst for arylation of conjugated alkenes
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A highly active and stereoselective heterogenised homogeneous catalyst montmorilloniteethylsilydiphenylphosphinepalladium (II) chloride complex (Pd/P is 1:1) for arylation of conjugated alkenes is reported.
- Choudary, Boyapati M.,Sarma, Ravichandra M.,Rao, Koteswara K.
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p. 719 - 726
(2007/10/02)
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- Ring-Splitting of 2,2-Diarylthiethane by Electron-Transfer Photosensitization of 9,10-Dicyanoanthracene
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A 9,10-dicyanoanthracene (DCA)-photosensitized reaction of 3-cyano- or 3-ethoxy-2,2-diarylthietane in acetonitrile gave selectively 2-cyano- or 2-ethoxy-1,1-diarylethene.The ring-splitting reaction proceeds via a one-electron oxidation of the sulfur atom of thietane ring by a photochemical electron transfer to the excited singlet state of DCA.
- Shima, Kensuke,Sazaki, Akira,Nakabayashi, Kenichi,Yasuda, Masahide
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p. 1472 - 1474
(2007/10/02)
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- A New Version of the Peterson Olefination Using Bis(trimethylsilyl)methyl Derivatives and Fluoride Ion as Catalyst
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Reaction between a variety of bis(trimethylsilyl)methyl derivatives and carbonyl compounds under fluoride ion as catalyst is described.The reaction works especially well with nonenolizable carbonyl compounds to give the expected alkenes in high yields and, in some cases, with high stereoselectivity.Application of this methodology to an intramolecular alkenation providing a tricyclic benzocarbacephem ring system is also described.
- Palomo, Claudio,Aizpurua, Jesus M.,Garcia, Jesus M.,Ganboa, Inaki,Cossio, F. P.,et al.
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p. 2498 - 2503
(2007/10/02)
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- Reaction of α-Substituted β-Bromostyrenes with Dicarbonyldicyanonickelate(0) Anion in Alkaline Medium under Carbon Monoxide
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The reactions of (E)- and (Z)-β-bromostyrene (1a) with dicarbonyldicyanonickelate(0) anion generated in situ in the presence of sodium or calcium hydroxide under carbon monoxide gave a carbonylated product mixture of (E)-cinnamic acid , 3,4-diphenylhexanedioic acid (4), and 3-phenylpropionic acid (5).In contrast, in the reactions of α-methyl- and phenyl-β-bromostyrenes (1b and c) the corresponding nitriles (3b and c) were formed, together with the carboxylic acids (2b and c).
- Miura, Masahiro,Shimoura, Nobuhiro,Nomura, Masakatsu
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p. 1993 - 1996
(2007/10/02)
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- STEREOCHEMICAL COURSE OF THE PALLADIUM-CATALYSED ARYLATION OF DISUBSTITUTED ACTIVATED ALKENES WITH BENZOYL CHLORIDE
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The palladium-catalysed arylation of ten 1,1- and 1,2-disubstituted activated alkenes with benzoyl chloride was studied.In most cases, more than one product was formed.The stereochemical course of the arylation appears to be controlled by the polarity of
- Spencer, Alwyn
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p. 209 - 216
(2007/10/02)
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- Crown Cation Complex Effects. 10. Potassium tert-Butoxide Mediated Penultimate Oxidative Hydrolysis of Nitriles
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The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions.An alternative hydrolysis method which involves potassium tert-butoxide mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented.The isolated yields reported here range from 21-93percent and are found to be highest for long-chain aliphatic nitriles such as cyanohexadecane.
- DiBiase, Stephen A.,Wolak, Raymond P.,Dishong, Dennis M.,Gokel, George W.
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p. 3630 - 3634
(2007/10/02)
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- Synthesis and pharmacological study of diphenylalkylamines with cycloaliphatic residues; new coronary vasodilators
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The paper describes the synthesis and the pharmacological evaluation of some derivatives of prenylamine, all with a cycloaliphatic ring within or instead of the isopropylamine moiety. Where the alicyclic ring had a bulky substituent in para were more active than prenylamine as coronary vasodilators on isolated guinea pig heart (Langendorff). The most interesting derivative was MG 8926 [N (3,3 diphenylpropyl) α methyl β cyclohexylethylamine], which was more active than prenylamine on Langendorff's heart and in enhancing the pressor response to catecholamines and inhibiting the isoprenaline induced hypotension. Moreover, it had almost the same effects as prenylamine as spasmolytic, local and general anesthetic, on heart rate and arterial pressure and against coronary spasm from pitressin.
- Carenini,Carissimi,Gentili,Grumelli,Picciola,Ravenna
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p. 2127 - 2136
(2007/10/06)
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