- Synthesis and antimicrobial evaluation of arylated 1,3,5-triphenyl pyrazoline derivatives using suzuki-miyaura reactions
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The first palladium –catalyzed coupling reactions of 1,3,5-triphenyl pyrazoline are reported. The Suzuki-Miyaura reaction of 3-(4-bromophenyl)-1,5-diphenyl pyrazoline with one equivalent of arylboronic acids afforded 3-(biphenyl)-1,5-diphenyl pyrazoline in 53-78 % yield. While the Suzuki-Miyaura reactions of 3,5-bis(4-bromophenyl)-1-phenyl pyrazoline with two equivalent of arylboronic acids gave 3,5-bis(biphenyl)-1-phenyl pyrazoline in 55-80% yield. The characterization of the synthesized derivatives (5a-h) and (6a-h) were accomplished on the basis of NMR, FT-IR, and mass techniques. The newly pyrazoline derivatives have been investigated for their in vitro antibacterial activity against gram- negative and gram-positive bacteria. The di-coupling compounds (6a-h) exhibited promising antibacterial against all four bacterial strains compared to the mono-coupling compounds (5a-h) which displayed a slight activity. The compound 6d showed a potent activity significantly more active than Trimethoprim (100μg/ml).
- Karim, Diana Khaled,Salman, Ghazwan Ali,Al-Mansury, Sadiq,Jinzeel, Nahida Abdulla
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p. 2469 - 2481
(2021/05/11)
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- Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties
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The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.
- Rocchi, Damiano,González, Juan F.,Gómez-Carpintero, Jorge,González-Ruiz, Víctor,Martín, M. Antonia,Sridharan, Vellaisamy,Menéndez, J. Carlos
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p. 722 - 731
(2018/10/20)
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- Synthesis of symmetrical and unsymmetrical triarylpyrylium ions: Via an inverse electron demand Diels-Alder reaction
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BF3·OEt2 mediated inverse electron demand Diels-Alder (IEDDA) reaction of chalcones with aryl acetylenes is reported for the synthesis of symmetrical and unsymmetrical 2,4,6-triarylpyrylium ions. The protocol provides an effective one-pot method for the utilization of readily available simple substrates under mild reaction conditions leading to a diverse array of pyrylium ions in moderately good yield.
- Fathimath Salfeena,Basavaraja,Ashitha,Kumar, V. Praveen,Varughese, Sunil,Suresh, Cherumuttathu H.,Sasidhar
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supporting information
p. 12463 - 12466
(2018/11/20)
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- Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway
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An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.
- Rehan, Mohammad,Maity, Sanjay,Morya, Lalit Kumar,Pal, Kaushik,Ghorai, Prasanta
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supporting information
p. 7728 - 7732
(2016/07/07)
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- Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent
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A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.
- Pathe, Gulab Khushalrao,Ahmed, Naseem
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supporting information
p. 3542 - 3552
(2015/11/17)
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- Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions
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A polyethyleneimine-supported triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene product in situ. In these transformations, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for activating trichlorosilane in the subsequent reduction reaction.
- Xia, Xuanshu,Toy, Patrick H.
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supporting information
p. 1737 - 1743
(2015/07/20)
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- Covalent Dimers of 1,3-Diphenylisobenzofuran for Singlet Fission: Synthesis and Electrochemistry
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Abstract The synthesis of covalent dimers in which two 1,3-diphenylisobenzofuran units are connected through one phenyl substituent on each is reported. In three of the dimers, the subunits are linked directly, and in three others, they are linked via an
- Akdag, Akin,Wahab, Abdul,Beran, Pavel,Rulí?ek, Lubomír,Dron, Paul I.,Ludvík, Ji?í,Michl, Josef
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- A general, mild and efficient palladium-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones: Bromo-chalcones a new coupling partner in cross-coupling reaction
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An efficient protocol for Pd-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones has been developed. We unveil a fascinating insight into the Pd-catalyzed C-O cross-coupling reaction. Pd/tBuXPhos (L1) ligand system facilitates the C-O cross-coupling reaction between 2,2,2-trifluoroethanol and activated aryl bromides at both higher (115 °C) and lower temperatures (40 °C). Unprecedentedly, this catalyst system facilitates the C-O cross-coupling reaction in short span of reaction times, generally 5-25 min (at 115 °C). The structurally simple analogue of tBuXPhos ligand so called JohnPhos (L2) ligand is also facilitated the C-O bond formation with activated aryl bromides and bromo-chalcones. Interestingly, under the optimal conditions (L1), methanol is also coupled rapidly with activated aryl bromides. These catalyst systems (L1 and L2) fail to couple electron rich aryl bromides with 2,2,2-trifluoroethanol, thus these catalyst systems allow the reductive elimination through an electronic pathway of reductive elimination. The unusual reactivity of 2,2,2-trifluoroethanol in Pd-catalyzed C-O cross-coupling reaction makes that the chemistry of fluorinated molecules is unique than that of non-fluorinated analogues. The bromo-chalcones can be used as a new coupling partner in the cross-coupling reaction.
- Rangarajan,Devi, Kavita,Ayushee,Prasad, Ashok K.,Pal Singh, Rishi
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p. 8307 - 8314
(2015/10/05)
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- Montmorillonite clay-promoted, solvent-free cross-aldol condensations under focused microwave irradiation
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An environmentally benign, clean and general protocol was developed for the synthesis of aryl and heteroaryl trans-chalcones. This method involved solvent-free reaction conditions under microwave irradiation in the presence of a clay-based catalyst, and afforded the target compounds in good yields and short reaction times. Furthermore, the same conditions allowed the synthesis of symmetrical, diarylmethylene-a,a-unsaturated ketones from aromatic aldehydes and ketones.
- Rocchi, Damiano,Gonzalez, Juan F.,Menendez, J. Carlos
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supporting information
p. 7317 - 7326
(2014/07/08)
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- Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles
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A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.
- Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
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supporting information
p. 946 - 950
(2014/04/03)
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- Allylic activation across an Ir-Sn heterobimetallic catalyst: Nucleophilic substitution and disproportionation of allylic alcohol
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A nucleophilic substitution of allylic alcohols with carbon (arene, heteroarene, allyltrimethylsilane, and 1,3-dicarbonyl compound), sulfur (thiol), oxygen (alcohol), and nitrogen (sulfonamide) nucleophiles has been demonstrated using an in house developed [Ir(COD)(SnCl3)l(μ-Cl)]2 heterobimetallic catalyst in 1,2-dichloroethane to afford the corresponding allylic products in moderate to excellent yields. In 4-hydroxycoumarin, allylation occurs at the 3-position. The diaryl-substituted allylic alcohols undergo disproportionation in presence of the heterobimetallic catalyst to provide the corresponding alkenes and chalcones. An electrophilic mechanism is proposed from Hammett correlation study.
- Chatterjee, Paresh Nath,Roy, Sujit
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supporting information; experimental part
p. 3776 - 3785
(2012/07/14)
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- Gold(I) complexes of brominated azadipyrromethene ligands
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Azadipyrromethenes are luminescent, red-light absorbing dyes that readily bind BF2+ and metals. Their framework allows for structural modification at the phenyl arms and the two pyrrolic carbon positions. Here we report five new gold
- Gao, Lei,Deligonul, Nihal,Gray, Thomas G.
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scheme or table
p. 7682 - 7688
(2012/09/05)
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- Electrophilicities of symmetrically substituted 1,3-diarylallyl cations
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Kinetics of the reactions of nine symmetrically substituted 1,3-diarylallyl cations with different nucleophiles were studied photometrically in dichloromethane, acetonitrile, and DMSO solutions. The second-order rate constants k2 were found to follow the correlation log k2 = sN(N + E). The electrophilicity parameters E of the title cations were derived, using the known values of sN and N of the nucleophilic reaction partners, and compared with the electrophilicities of analogously substituted benzhydrylium ions. Good linear correlations were found between the electrophilicities E and the quantum chemically calculated gas-phase methyl anion affinities of the allyl cations and the σ+ constants of the substituents X.
- Troshin, Konstantin,Schindele, Claus,Mayr, Herbert
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experimental part
p. 9391 - 9408
(2012/01/06)
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- Etherification of darylmethanols and 1-phenylalkan-1-ols over platinum on carbon
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In the presence of platinum on carbon (Pt/C), diarylmethanols and donor substituted 1-phenylalkan-1-ols undergo cross-etherification with primary and secondary alcohols.
- Thiemann, Thies
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experimental part
p. 515 - 525
(2010/04/23)
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- Process for preparing vinyl substituted beta-diketones
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A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.
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Page/Page column 7
(2008/06/13)
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- Synthesis of vinyl-substituted β-diketones for polymerizable metal complexes
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Polymerizable β-diketones for application to metal ion coordination have been prepared and characterized. Bromine-substituted β-diketones were synthesized under Claisen-Schmidt-type condensation conditions. Vinyl groups were substituted for the halide by
- Southard, Glen E.,Murray, George M.
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p. 9036 - 9039
(2007/10/03)
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- ELECTROLUMINESCENT DEVICE
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Disclosed are electroluminescent devices that comprise organic layers that contain certain organic compounds containing one ore more pyrimidine moieties. The organic compounds containing one ore more pyrimidine moieties are suitable components of blue-emi
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- Synthesis and antifungal activity of 1,3-bis(4-methyl/4-bromo/3-nitrophenyl) propan-1,3-diones and their 2 analogs
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The reaction of substituted acetophenones (1-3) with 4-methyl-, 4-bromo- or 3-nitrobenzaldehyde (4-6) in ethanolic NaOH gives the correponding 1,3-bis(4-methyl/4-bromo/3-nitrophenyl)-2-propen-1-ones (7-9) in good yields, which on bromination yield substit
- Suman, Mrs.,Singh, Rajvir,Malik, M. S.,Kathpal, T. S.,Malik, O. P.
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p. 743 - 746
(2007/10/03)
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