- Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazine derivatives
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The aim of this study is to obtain new unsaturated piperazine compounds by the reactions of piperazine (1a) and piperazine derivatives (1b–1d) with acylation reactive groups (2a–2j). Methacryloyl piperazine (1b) was synthesized from the reaction of methacrylic anhydride with piperazine (1a). Acyl chlorides (2b–2d) were prepared from the reaction of thionyl chloride with carboxylic acids (3a–3c) obtained as a result of the reaction with malonic acid and suitable aldehyde (5-methylfuran-2-carbaldehyde for 3a, cinnamaldehyde for 3b, and thiophene-2-carbaldehyde for 3c), respectively, by literature methods. Acyl chlorides 2e and 2f were obtained from the reaction of commercially purchased carboxylic acids 3d and 3e with thionyl chloride. Acyl chlorides (2g–2j) were synthesized from the reaction of thionyl chloride with carboxylic acids (3d–3g) transformed from hydrolyzation of esters (4a–4d) obtained as a result of the reaction of triethyl phosphonoacetate with a suitable ketone (acetophenone for 4a, benzophenone for 4b, 1-(5-methylfuran-2-yl)ethan-1-one for 4c, and 1-(thiophen-2-yl)ethan-1-one for 4d), respectively, by literature methods. Unsaturated piperazine derivatives 5a and 5b were obtained from the reaction of 1b with 2b and 2e, respectively. In addition, from the reaction of 1b and acyl chlorides (2b–2j), unsaturated piperazines (5c–5k) were synthesized in medium to good yields (63%–84%). Also, 5l–5g and 5r–5w were obtained from the reaction of allyl piperazine (2c) and cinnamyl piperazine (2d) with acyl chlorides (2a–2f).
- Sari, Sait,ünalan, Seda,Yilmaz, Mehmet
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p. 1656 - 1671
(2020/01/03)
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- α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric exo-Selective 1,3-Dipolar Cycloaddition with Nitrones
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1,3-Dipolar cycloaddition is a commonly exploited method to access 5-membered chemical entities with a variety of peripheral functionalities and their stereochemical arrangements. Nitrones are isolable 1,3-dipoles that exhibit sufficient reactivity toward electron-deficient olefins in the presence of Lewis acids to deliver highly substituted isoxazolidines. Herein we document that α,β-unsaturated amides, generally regarded as barely reactive in a 1,3-dipolar reaction manifold, were effectively activated using the designed 7-azaindoline auxiliary in an In(OTf)3/bishydroxamic acid catalytic system. The broad substrate scope and clean removal of the 7-azaindoline auxiliary from the product highlight the synthetic utility of the present catalysis.
- Zhang, Ming,Kumagai, Naoya,Shibasaki, Masakatsu
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p. 12450 - 12455
(2017/09/18)
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- Traceless directing group mediated branched selective alkenylation of unbiased arenes
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Owing to the synthetic importance of branched olefinated products, we report palladium catalyzed formation of branched olefins facilitated by a C-H activation based protocol. This involves selective insertion of olefins and subsequent decarboxylation using a completely unbiased benzene ring as the starting precursor. The significance of the protocol has been further highlighted by exhibition of functionality tolerance along with a late-stage modification of the branched olefinated products leading to the formation of other functionalized molecules.
- Agasti, Soumitra,Dey, Aniruddha,Maiti, Debabrata
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supporting information
p. 12191 - 12194
(2016/10/21)
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- Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
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Pd-catalyzed α-olefinic C-H activation of simple α,β-unsaturated olefins has been developed. 4-imino-β-lactam derivatives were readily synthesized via activation of α-olefinic C-H bonds with excellent cis stereoselectivity. A wide range of heterocycles at the β-position are compatible with this reaction. The product of 4-imino-β-lactam derivatives can be readily converted to 2-aminoquinoline which exists extensively in pharmaceutical drugs and natural products.
- Kong, Wei-Jun,Liu, Yue-Jin,Xu, Hui,Chen, Yan-Qiao,Dai, Hui-Xiong,Yu, Jin-Quan
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p. 2146 - 2149
(2016/03/05)
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- Hydroxamic acids block replication of hepatitis c virus
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Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.
- Ai, Teng,Xu, Yanli,Qiu, Li,Geraghty, Robert J.,Chen, Liqiang
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p. 785 - 800
(2015/01/30)
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- Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate
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Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles in presence of manganese(III) acetate produced ethyl 4-cyano-2,3-dihydrofuran-3-carboxylates and 4-cyano-2,3-dihydrofuran-3- carboxamides in good yields. The radical cyclizations of conjugated amides gave 2,3-dihydrofurans in better yields than that of conjugated esters. Moreover, the reactions of thienyl substituted amides and esters with 3-oxopropanenitriles afforded 2,3-dihydrofurans more efficiently than phenyl substituted ones. ARKAT-USA, Inc.
- Yilmaz, E. Vildan Burgaz,Yilmaz, Mehmet,Oektemer, Atilla
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p. 363 - 376
(2011/09/20)
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- Palladium-catalyzed intramolecular amidation of C(sp2)-H bonds: Synthesis of 4-aryl-2-quinolinones
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Figure presented A catalytic synthetic approach for the synthesis of 2-quinolinone compounds through a Pd-catalyzed C(sp2)-H functionalization/intramolecular amidation sequence is described. The cyclization process efficiently proceeds in the p
- Inamoto, Kiyofumi,Saito, Tadataka,Hiroya, Kou,Doi, Takayuki
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supporting information; experimental part
p. 3900 - 3903
(2010/07/05)
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- Synthesis of β-, γ-, and δ-lactams via Pd(II)-catalyzed C-H activation reactions
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Pd(II)-catalyzed intramolecular amination of sp2 and sp3 C-H bonds are developed using a combination of CuCl2 and AgOAc as the oxidant. The reaction protocol tolerates the presence of a double bond in the substrates. This catalytic reaction provides practical access to a wide range of β-, γ-, and δ-lactams. Copyright
- Wasa, Masayuki,Yu, Jin-Quan
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supporting information; experimental part
p. 14058 - 14059
(2009/03/11)
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- N-(4-(4-(2-halogenophenyl)piperazin-1-yl)butyl) substituted cinnamoyl amide derivatives as dopamine D2 and D3 receptor ligands
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A series of eight substituted N-(4-(4-(2-halogenophenyl)piperazin-1-yl) butyl)-3-phenylacryl amide derivatives have been synthesized and screened for binding affinities at dopamine hD2 and hD3 receptors. All compounds have shown high
- Saur, Oliver,Hackling, Anneke E.,Perachon, Sylvie,Schwartz, Jean-Charles,Sokoloff, Pierre,Stark, Holger
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p. 178 - 184
(2008/02/09)
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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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- Chemoselectivity in the rhodium(II) acetate catalysed decomposition of α-diazo-β-keto-γ,δ-alkenyl-δ-aryl compounds: Aromatic C-H insertion reaction or Wolff rearrangement-electrocyclization
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The rhodium(II) acetate catalysed decomposition of α-diazo-β-keto-γ,δ-alkenyl phosphonates 1 substituted in the δ-position by an aryl group gave rise to mixtures of isomeric hydroxynaphthalenephosphonates, 3 resulting from a Wolff rearrangement-electrocyc
- Collomb, Didier,Chantegrel, Bernard,Deshayes, Christian
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p. 10455 - 10472
(2007/10/03)
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- N-ACRYLOYLPIPERAZINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS PAF ANTAGONISTS
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Compounds of formula (I): STR1 wherein R 1 and R 2 is each--R 5,--CH=CH--R 5 or--C C--R 5, wherein R. sup.5 is optionally substituted aryl or aromatic heterocyclic; R 3 is hydrogen, alkyl, cyano or--R 5 ; X is oxygen or sulfur; A is 1,4-piperazin-1, 4-diyl or a 1,4-homopiperazin-1,4-diyl; B' is alkylene, carbonyl, thiocarbonyl, sulfinyl or sulfonyl; and R 4 is optionally substituted phenyl and pharmaceutically acceptable salts thereof have valuable PAF antagonist activity, and may be prepared by reacting a compound containing the piperazine or homopiperazine part of the molecular with a compound containing the other part of the molecule.
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