3003-84-7Relevant academic research and scientific papers
Stereoselective synthesis, natural occurrence and CB2 receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp.
Matovic,Matthias,Gertsch, Juerg,Raduner, Stefan,Bone,Lehmann,DeVoss
, p. 169 - 174 (2007)
A divergent synthesis of (2E,4E,8E,10E)- and (2E,4E,8E,10Z)-N- isobutyldodeca-2,4,8,10-tetraenamides from pent-4-yn-1-ol allowed identification of the (2E,4E,8E,10Z)-isomer for the first time in Echinacea species. A short, stereoselective synthesis of the (2E,4E,8E,10Z)-isomer is also described which allowed further biological evaluation of this material, and the demonstration that this isomer does not occur in Spilanthes mauritiana as previously reported. This journal is The Royal Society of Chemistry.
Chemoenzymatic Halocyclization of γ,δ-Unsaturated Carboxylic Acids and Alcohols
Younes, Sabry H. H.,Tieves, Florian,Lan, Dongming,Wang, Yonghua,Süss, Philipp,Brundiek, Henrike,Wever, Ron,Hollmann, Frank
, (2019/12/27)
A chemoenzymatic method for the halocyclization of unsaturated alcohols and acids by using the robust V-dependent chloroperoxidase from Curvularia inaequalis (CiVCPO) as catalyst has been developed for the in situ generation of hypohalites. A broad range of halolactones and cyclic haloethers are formed with excellent performance of the biocatalyst.
Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols
Borukhova, Svetlana,Nol, Timothy,Hessel, Volker
, p. 67 - 74 (2016/01/16)
Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1. The incredible bulk: Bulk alcohols are converted continuously into chlorides using HCl in a microflow. A reaction network that consists of four steps and two inline separations leads to the continuous preparation of cinnarizine, cyclizine, and a buclizine derivative with yields of 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1.
Gold(I)-, palladium(II)-, platinum(II)-, and mercury(II)-catalysed spirocyclization of 1,3-enynediols: Reaction scope
Zhdanko, Alexander,Maier, Martin E.
supporting information, p. 3411 - 3422 (2014/06/09)
The spirocyclization of different 1,3-enynediols was investigated. The reaction was only efficient for the synthesis of [5,6]-spiroacetals. In this case, the reaction was characterized by almost quantitative yields, short reaction times, and low catalyst loadings (0.5-1%). When the synthesis of [6,6]-spiroacetals was attempted, the reaction suffered from poor regioselectivity and a higher propensity of the intermediate dienol ethers to decompose under the acidic conditions, and it became no longer viable. But it is possible to generate the dienol ethers cleanly under milder conditions as a mixture of regioisomers. This striking difference in reaction efficiency was explained by the unstable dienol ethers cyclizing more quickly to give [5,6]-spiroacetals than to give [6,6]-spiroacetals. In this study, the successful application of a new cationic palladium pincer complex for electrophilic alkyne activation at room temperature has been demonstrated for the first time. Copyright
Synthesis of C3-C9-alkenyl 2,3-unsaturated glucosides from glucose and some alkenols
Konstantinovic,Predojevic,Gojkovic,Ratkovic,Dimitrijevic,Mojsilovic
, p. 802 - 805 (2007/10/03)
C3-C9-Alkenyl 2,3-unsaturated glucosides have been synthesized from glucose and C3-C9-alkenols by using Ferrier reaction with boron trifluoride etherate (BF3·Et2O) as Lewis acid catalyst in key step.
Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration
Chaudhari, Sachin S.,Akamanchi, Krishnacharya G.
, p. 1763 - 1765 (2007/10/03)
A solution of 1:1 equivalent of thionyl chloride and benzotriazole in dry methylene chloride efficiently transforms alcohols and carboxylic acids into the corresponding alkyl chlorides and acid chlorides respectively at room temperature, with excellent yields by simple titration.
A Novel Method for the Conversion of Halide Anion to the Positive Halogen by Nitrobenzenesulfonyl Peroxide. Application to Oxyhalogenation of Olefin
Yoshida, Masato,Mochizuki, Hideki,Suzuki, Takashi,Kamigata, Nobumasa
, p. 3704 - 3706 (2007/10/02)
Bromide and chloride anions could be readily oxidized into positive halogens by treating with p-nitrobenzenesulfonyl peroxide.The positive halogens, thus formed, reacted with olefins to give epihalonium ions, which were trapped by oxygen nucleophiles inter- or intramolecularly to afford oxyhalogenated compounds.
Novel pesticides, preparation and use
-
, (2008/06/13)
The specification describes and claims methods of controlling acarine pests by application of a compound of Formula (I), methods of controlling arthropod pests by application of a compound of Formula (IA), compounds of Formula (IA) per se, pesticidal compositions comprising a compound of Formula (IA), and processes for preparing a compound of Formula (IA).
Cyclisation de composes acetyliniques carbonyles via leur ether d'enol silyle: II. Synthese et reactivite de quelques ethers d'enols derivees d'aldehydes ou de cetones acetyleniques terminaux
Boaventura, Maria-Amelia,Drouin, Jacques
, p. 1015 - 1026 (2007/10/02)
A number of silyl enol ethers of ω-acetylenic ketones or aldehydes have been prepared following various literature procedures which are compared to each other.By treatment with mercury (II) chloride (1.1 equiv.) in the presence of HMDS (0.2 or 1.5 equiv.) at room temperature, followed by acidification with aqueous HCl-NaI, silyl enol ethers 1, 2, 3, 9, 11, 12 and 13 are cyclized in high yield into 2-alkylidene-1-oxocyclopentanes, methylene- spiro or poly-cyclanones, a methylene cyclopentane unit being formed in the reaction.In the same way, from silyl enol ethers 4, 8 and 10 a methylenecyclohexane unit is formed.In all the products the exocyclic position of the C=C double bond so formed is fully maintained.
SYNTHESE ET REACTIVITE DE SILANES PROPARGYLIQUES ω-FONCTIONNELS : PREPARATION DE VINYLIDENE-3 OXOLANNES, OXANNES, OXEPANNES ET OXOCANNES
Pornet, J.,Damour, D.,Miginiac, L.
, p. 2017 - 2024 (2007/10/02)
The ω-silyloxypropargyltrimethylsilanes regiospecifically react with aliphatic and aromatic aldehydes to lead to vinylidene oxigen-containing heterocycles, such as 3-vinylidene oxolanes, oxanes, oxepanes and oxocanes.
