134419-77-5Relevant academic research and scientific papers
Microwave-assisted coupling reaction by copper(I)-catalyzed of terminal alkynes with aroyl chlorides
Wang,Wei,Hu,Liu,Fu
, p. 3527 - 3532 (2001)
A rapid and efficient method for synthesis of α,β-conjugated acetylenic ketones involves reaction of phenylacetylene with aroyl chlorides in the presence of catalytic amount CuI under microwave irradiation to give the corresponding α,β-conjugated acetylen
Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt
Sweet, Jamie S.,Rajkumar, Sundaram,Dingwall, Paul,Knipe, Peter C.
supporting information, p. 3980 - 3985 (2021/03/31)
Inspired by naturally occurring molecules containing atropisomeric N+-C axes, we have developed a novel synthetic approach to generate a library of axially chiral N-aryl quinolinium salts. Enantiopurities up to 93 % ee were obtained via a four-step route from commercially available precursors. Axial stereochemistry was controlled through an enantioselective ring-closing Buchwald–Hartwig coupling reaction. The structure and properties of the salts were examined by X-ray crystallography, DFT, UV-Vis, and fluorescence spectroscopy, revealing high rotational barriers and solvatochromic behaviour.
Synthesis of Dibenzotropones by Alkyne-Carbonyl Metathesis
Ehlers, Peter,Frey, Anna,Langer, Peter,Rettmann, Andre,Sobhani, Maryam,Thom, Richard,Villinger, Alexander
supporting information, p. 14420 - 14432 (2021/11/16)
Dibenzocycloheptanones (dibenzotropones) were prepared by Br?nsted acid mediated intramolecular alkyne-carbonyl metathesis (ACM) reactions. The cyclization precursors are readily available by Sonogashira reaction of 2-bromobenzoyl chloride with terminal alkynes, followed by Suzuki reactions with benzaldehydes. The ACM reactions are highly modular and atom economic and allow for the construction of two regioisomeric series of dibenzotropones.
Base-Promoted Synthesis of Polysubstituted 4-Aminoquinolines from Ynones and 2-Aminobenzonitriles under Transition-Metal-Free Conditions
Kumar, Ankit,Mishra, Pawan K.,Saini, Kapil Mohan,Verma, Akhilesh K.
supporting information, p. 2546 - 2551 (2021/03/16)
A transition-metal-free and base-promoted one-pot reaction of ynones with 2-aminobenzonitriles is described. The reaction was initiated through sequential aza-Michael addition/intramolecular annulation to afford various multisubstituted 4-aminoquinolines
Nickel (II) dibenzotetramethyltetraaza[14]annulene supported on DFNS nanoparticles catalyst in carbonylative sonogashira coupling
Mohsen Sadeghzadeh, Seyed,Tian, Shaopeng,Yang, Qianqian
, (2021/01/18)
In this study, the carbonylative sonogashira coupling reaction was performed in the presence of CO (2 MPa) and Nitmtaa?DFNS as NPs. Nickel(II)dibenzotetramethyltetraaza[14]annulene complex (Nitmtaa) prepared and immobilized on amino-fucntionnalized DFNS (N-DFNS) via Ni[sbnd]N (NH2) bond to obtain a stable and reusable new nanocatalyst named as Nitmtaa?DFNS. Good to superb performance products were provided deploying Nitmtaa?DFNS nanocatalyst. In addition, the anatomy of Nitmtaa?DFNS has been distinguished by various methods, including XRD, VSM, FT-IR, SEM, EDX, TEM, and TGA. In addition, the hot filtration test provided complete insight into the heterogeneity of the catalyst. The reuse and recycling of the catalyst were repeatedly investigated for coupling reactions. In addition, the mechanism of the coupling reactions was thoroughly studied.
A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives
Xie, Caixia,Yang, Di,Wang, Xinfeng,Ma, Chen
, p. 14937 - 14944 (2020/12/02)
A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.
Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives
Wang, Mengdan,Yang, Yajie,Song, Bo,Yin, Liqiang,Yan, Shuhui,Li, Yanzhong
supporting information, p. 155 - 159 (2020/01/03)
An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf
Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F
Mehta, Goverdhan,Nerella, Sharanya,Pabbaraja, Srihari,Singh, Shweta
supporting information, (2020/02/22)
An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.
Base-Promoted Michael Addition/Smiles Rearrangement/ N-Arylation Cascade: One-Step Synthesis of 1,2,3-Trisubstituted 4-Quinolones from Ynones and Sulfonamides
Liu, Jing,Ba, Dan,Lv, Weiwei,Chen, Yanhui,Zhao, Zemin,Cheng, Guolin
supporting information, p. 213 - 223 (2019/12/11)
A general, practical, and environmentally friendly protocol to synthesize 1,2,3-trisubstituted 4-quinolones from readily available ynones and sulfonamides was developed. The construction of one C?C bond and two C?N bonds via cleavage of one N?S, one C?S,
Synthesis of 3-(2-quinolyl) chromones from ynones and quinoline: N -oxides via tandem reactions under transition metal- And additive-free conditions
Liu, Jing,Ba, Dan,Chen, Yanhui,Wen, Si,Cheng, Guolin
supporting information, p. 4078 - 4081 (2020/04/20)
A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- and additive-free conditions a
