Branched 2-amino-1,3-dicyanocyclopenta-1,3-diene

Mapping Intimacies ◽

10.21203/rs.3.rs-294033/v1 ◽

2021 ◽

Author(s):

Francisco Ros

Keyword(s):

Cyano Group ◽

Cyclic Compound ◽

Electronic Configuration ◽

The Novel ◽

One Pot ◽

Strong Polarization ◽

Yellow Color ◽

Diene System

Abstract Reaction of 2-chloroisobutyrophenonewith two equivalents of malononitrile anion furnishes 2-amino-1,3-dicyano-5,5-dimethyl-4-phenylcyclopenta-1,3-diene. The cyclic compound represents the novel 2-amino-1,3-dicyanocyclopentadiene structure. The unique 1-cyano-2-amino-3-cyano arrangement in the cyclopentadiene brings about a strong polarization of the electronic configuration of the diene system that is conformed by two opposite dipolar halves. The polarized electronic configuration accounts for the extreme persistence manifested by the cyclopentadiene. The compound owns a vivid lemon-hued yellow color consequent to an unusually intense n ®p*absorption of a cyano group in the extensively conjugated compound. This is built up by consecutive one-pot reaction of two molecules of malononitrile carbanion and the ketonic substrate followed by a new tandem carbon-carbon cyclization with final elimination of cyanate ion.

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The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale

Molecular Catalysis ◽

10.1016/j.mcat.2021.111532 ◽

2021 ◽

Vol 506 ◽

pp. 111532

Author(s):

Fatemeh Mohammadi Metkazini ◽

Zahra Khorsandi ◽

Akbar Heydari

Keyword(s):

Carbon Disulfide ◽

Large Scale ◽

Recyclable Catalyst ◽

The Novel ◽

Efficient Synthesis ◽

Acid Base ◽

One Pot ◽

Trapping Process ◽

Magnetic Recyclable

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One-Pot Synthesis of 7, 7-Dimethyl-4-Phenyl-2-Thioxo-2,3,4,6,7, 8-Hexahydro-1H-Quinazoline-5-OnesUsing Zinc Ferrite Nanocatalyst and Its Bio Evaluation

Catalysts ◽

10.3390/catal11040431 ◽

2021 ◽

Vol 11 (4) ◽

pp. 431

Author(s):

Tentu Nageswara Rao ◽

Nalla Krishnarao ◽

Faheem Ahmed ◽

Suliman Yousef Alomar ◽

Fadwa Albalawi ◽

...

Keyword(s):

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

Zinc Ferrite ◽

Large Scale ◽

Cyano Group ◽

Proton Nuclear Magnetic Resonance ◽

Scale Production ◽

One Pot ◽

Antibacterial And Antifungal ◽

Nuclear Magnetic

A simple and highly efficient protocol for the synthesis of derivatives 7, 7-dimethyl-4-phenyl-2-thioxo-2, 3, 4, 6, 7, 8-hexahydro-1H-quinazoline-5-one from 5, 5-dimethyl cyclohexane-1, 3-dione (4a–4h) (dimedone) has been described. The aryl aldehydes were substituted with thiourea in the presence of synthesized zinc ferrite nanocatalyst, which increased the yield under reflux through condensation, followed by cyclization to give desired products. The other advantages are that it is eco-friendly and economically affordable for large-scale production. Structural validation and characterization of all the newly synthesized compounds were evaluated by spectral analysis (mass spectrometry, proton nuclear magnetic resonance (1HNMR), and Carbon-13 nuclear magnetic resonance(13CNMR)spectroscopies. The structure of antibacterial and antifungal assays was performed with the newly synthesized compounds. The antimicrobial activity of title compounds possessing electron-withdrawing groups such as (4e–4h) (Cl, Br, and cyano group) exhibited more active potential than the electron-donating groups, C6H5,4-C6H4, 3-OC2H5-4OH-C6H3, etc., (4a–4d) containing moiety.

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One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽

10.3390/molecules26051466 ◽

2021 ◽

Vol 26 (5) ◽

pp. 1466

Author(s):

Ye Eun Kim ◽

Hyunsung Cho ◽

Yoo Jin Lim ◽

Chorong Kim ◽

Sang Hyup Lee

Keyword(s):

Alkyl Halide ◽

The Novel ◽

Reaction Conditions ◽

One Pot ◽

One Pot Synthesis ◽

Consecutive Reactions ◽

Intramolecular Condensation ◽

Synthetic Sequence ◽

Novel Target

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.

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Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium

Synthesis ◽

10.1055/s-0036-1591849 ◽

2017 ◽

Vol 50 (03) ◽

pp. 565-574 ◽

Cited By ~ 9

Author(s):

Norio Sakai ◽

Shuhei Horikawa ◽

Yohei Ogiwara

Keyword(s):

Catalytic System ◽

Elemental Sulfur ◽

Direct Conversion ◽

The Novel ◽

One Pot

The direct conversion of lactones into thiolactones with elemental sulfur (S8) catalyzed by InCl3/PhSiH3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.

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Mussel-Inspired Co-Deposition of Polydopamine/Silica Nanoparticles onto Carbon Fiber for Improved Interfacial Strength and Hydrothermal Aging Resistance of Composites

Polymers ◽

10.3390/polym12030712 ◽

2020 ◽

Vol 12 (3) ◽

pp. 712 ◽

Cited By ~ 2

Author(s):

Xuejun Cui ◽

Lichun Ma ◽

Guangshun Wu

Keyword(s):

Carbon Fibers ◽

Interfacial Strength ◽

Fiber Surface ◽

The Novel ◽

Hydrothermal Aging ◽

One Pot ◽

Polar Groups ◽

Aging Resistance ◽

Interfacial Compatibility ◽

Hydrolysis Of

A novel and effective strategy was first proposed for the codeposition of a mussel-inspired nanohybrid coating with excellent wettability onto the surface of carbon fibers (CFs) by simultaneous polymerization of bioinspired dopamine (DA) and hydrolysis of commercial tetraethoxysilane (TEOS) in an eco-friendly one-pot process. Mussel-inspired nanohybrids could be adhered onto the surface of CFs firmly. The novel modification could afford sufficient polar groups and significantly improve fiber surface roughness and energy without decreasing fiber intrinsic strength, which were advantageous to promote interfacial compatibility and wettability between CFs and matrix resin. As a result, the interfacial shear strength of composites increased to 48.21 ± 1.45 MPa compared to that of untreated composites 29.47 ± 0.88 MPa. Meanwhile, the nanohybrid coating increased significantly composites’ hydrothermal aging resistance. The efficient strategy shows a promising and green platform of surface functionalization of CFs for preparing advanced polymer composites arising from broadly mechanical-demanding and energy-saving usages.

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A Solvent-Mediated Excited-State Intermolecular Proton Transfer Fluorescent Probe for Fe3+ Sensing and Cell Imaging

Molecules ◽

10.3390/molecules27020516 ◽

2022 ◽

Vol 27 (2) ◽

pp. 516

Author(s):

You Qian ◽

Fuchun Gong ◽

Jiguang Li ◽

Pan Ma ◽

Hanming Zhu ◽

...

Keyword(s):

Excited State ◽

Proton Transfer ◽

Fluorescent Probe ◽

Cell Imaging ◽

Cyano Group ◽

Proton Donor ◽

Cell Permeability ◽

One Pot ◽

Intermolecular Proton Transfer ◽

Synthesis Strategy

Constructing excited-state intermolecular proton transfer (ESIPT-e) fluorophores represents significant challenges due to the harsh requirement of bearing a proton donor-acceptor (D-A) system and their matching proton donating-accepting ability in the same molecule. Herein, we synthesized a new-type ESIPT-e fluorophor (2-APC) using the “four-component one-pot” reaction. By the installing of a cyano-group on pyridine scaffold, the proton donating ability of -NH2 was greatly enhanced, enabling 2-APC to undergo ESIPT-e process. Surprisingly, 2-APC exhibited dual-emissions in protic solvents ethanol and normal fluorescence in aprotic solvents, which is vastly different from that of conventional ESIPT-a dyes. The ESIPT emission can be obviously suppressed by Fe3+ due to the coordination reaction of Fe3+ with the A-D system in 2-APC. From this basis, a highly sensitive and selective method was established using 2-APC as a fluorescent probe, which offers the sensitive detection of Fe3+ ranging from 0 to 13 μM with the detection limit of 7.5 nM. The recovery study of spiked Fe3+ measured by the probe showed satisfactory results (97.2103.4%) with the reasonable RSD ranging from 3.1 to 3.8%. Moreover, 2-APC can also exhibit aggregation-induced effect in poor solvent or solid-state, eliciting strong red fluorescence. 2-APC was also applied to cell-imaging, exhibiting good cell-permeability, biocompatibility and color rendering. This multi-mode emission of 2-APC is significant departure from that of conventional extended p-conjugated systems and ESIPT dyes based on a flat and rigid molecular design. The “one-pot synthesis” strategy for the construction of ESIPT molecules pioneered a new route to achieve tricolor-emissive fluorophores.

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Direct Cu Wet Seed on Barrier of TSV Wafer

Additional Conferences (Device Packaging HiTEC HiTEN & CICMT) ◽

10.4071/2010dpc-tp12 ◽

2010 ◽

Vol 2010 (DPC) ◽

pp. 000759-000773

Author(s):

Jianwen Han ◽

Xuan Lin ◽

Yun Zhang ◽

Joseph Aby ◽

Thierry Mourier

Keyword(s):

Thickness Distribution ◽

Electrochemical Process ◽

Nucleation Density ◽

The Novel ◽

Signal Delay ◽

Strong Polarization ◽

Seed Distribution ◽

Silicon Vias ◽

Connection Density

Through Silicon Vias (TSVs) promise to provide shorter interconnect length and higher electrical connection density with reduced signal delay and power consumption for both multichip interconnection and packaging. To achieve void free electrolytic TSV gapfill, continuous seed is critical. While the TSV dimension scales down and the aspect ratio increases, continuous Cu seed coverage is harder to achieve by conventional PVD process. Giving the conformal nature of electrochemical process, direct electrolytic Cu deposition on barrier is an alternative to enable continuous seed coverage. The challenges for direct wet seed are: (1) the barrier layer, typically TiN and TaNx, is too resistive to achieve uniform thickness distribution by conventional copper plating processes. (2) the nucleation of copper on barrier oxides is difficult and the copper growth is dendritic. Designed for direct seeding on barriers, a novel chemistry has been developed. This alkaline (pH 9~10) bath has been demonstrated with TSV wafers with different barriers including Ta, TaNx, Ti, TiN. The process has shown to provide high nucleation density (10Exp11~10Exp12 nuclei/cm2) and continuous seed coverage can be achieved between 10 and 25nm thickness on most barriers. The deposition takes place at very negative plating potential while the current efficiency is maintained at >90%. The strong polarization enables in-situ barrier oxide reduction for some barriers, and pretreatment becomes not necessary. Elimination of oxides along with high nucleation density significantly enhanced the bonding strength between copper and barriers. The wet seed on all barriers including Ta, TaNx, Ti, TiN has passed ASTM D3359 cross-cut tape test. Electrolytic TSV gapfill on the wet seed is demonstrated for patterned TiN barrier TSV wafer. Void-free fills are achieved for the features with dimensions between 20 and 200 microns. In summary, the novel chemistry for direct copper wet seed deposition on barriers has been demonstrated to yield high nucleation density and uniform seed distribution with adequate adhesion, and the wet seed enables subsequent void free TSV gapfill.

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Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl

Synthesis ◽

10.1055/s-0037-1610755 ◽

2020 ◽

Vol 52 (11) ◽

pp. 1707-1718

Author(s):

Nasser Etivand ◽

Jabbar Khalafy ◽

Mohammad G. Dekamin

Keyword(s):

Aqueous Media ◽

Thiobarbituric Acid ◽

Environmentally Benign ◽

The Novel ◽

One Pot ◽

Synthetic Strategy ◽

Three Component Reaction ◽

High Yields ◽

Green Procedure ◽

Arylglyoxal Monohydrates

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

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