790-10-3Relevant academic research and scientific papers
Asymmetric Synthesis of Hydroquinazolines Bearing C4-Tetrasubstituted Stereocenters via Kinetic Resolution of α-Tertiary Amines
Jiang, Qianwen,Qin, Tianren,Yang, Xiaoyu
supporting information, p. 625 - 630 (2022/01/20)
A novel protocol for asymmetric synthesis of hydroquinazolines bearing C4-tetrasubstituted stereocenters has been achieved through kinetic resolution of 2-amido α-tertiary benzylamines via chiral phosphoric acid catalyzed intramolecular dehydrative cyclizations. This method gave access to both α-tertiary benzylamines and hydroquinazolines with broad scope and high enantioselectivities. An intriguing restricted rotation of the C-N bond was observed for hydroquinazoline products bearing C4-tetrasubstituted stereocenters.
Synthesis of trifluoromethyl substituted nucleophilic glycine equivalents and the investigation of their potential for the preparation of α-amino acids
Bergagnini-Kolev, Mackenzie,Howe, Mitchell,Burgess, Emily,Wright, Payton,Hamburger, Samantha,Zhong, Zhennan,Ellis, Shawna B.,Ellis, Trevor K.
supporting information, (2020/12/02)
The synthetic preparation of several Ni(II) complexed Schiff Bases of glycine will be introduced, as well as investigations into their reactivity and utility. Key to these investigations is the incorporation of electron-withdrawing trifluoromethyl groups within the framework of the conjugated system that stabilizes the enolate derived from the glycine component. Reactivity was evaluated for each of the complexes under phase transfer catalyzed alkylations with hydroxide bases, as well as the DBU catalyzed Michael Additions of optically active 3′-substituted-2-oxazoladinone amides of unsaturated carboxylic acids. It was found that the trifluoromethyl containing nucleophilic glycine equivalents were more reactive than their non-trifluoromethyl analogues in both reaction types. Therefore, the application of these modified Ni(II) complexes of glycine Schiff Bases are useful for the preparation of α-amino acids through phase transfer catalyzed alkylation as well as the preparation of optically pure β-substituted pyroglutamic acid precursors.
One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization
Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min
supporting information, p. 2438 - 2455 (2020/01/31)
A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.
Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes
Li, Quanzhe,Liu, Jiaxin,Shi, Min,Wei, Yin
supporting information, (2020/03/26)
In this paper, we revealed a metal-free and visible light photoinduced method for the rapid construction of spirobi[indene] skeletons, providing a simple and efficient way for easy access to spirobi[indene] scaffolds under mild conditions along with a broad substrate scope and good functional group tolerance.
Pd-catalyzed regiodivergent synthesis of diverse oxindoles enabled by the versatile heck reaction of carbamoyl chlorides
Wu, Xianqing,Tang, Zaiquan,Zhang, Chengxi,Wang, Chenchen,Wu, Licheng,Qu, Jingping,Chen, Yifeng
supporting information, p. 3915 - 3921 (2020/06/08)
We report herein a miscellaneous oxindole synthesis bearing an all-carbon quaternary center, enabled by Pd-catalyzed intramolecular cyclization followed by multiple intermolecular Heck reactions of both easily accessible alkene-tethered carbamoyl chlorides and olefins. This protocol obviates the use of prefunctionalized olefinic reagents, exhibits excellent functional group tolerance, and features fascinating reactive versatility.
Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution
Li, Quanzhe,Yu, Liuzhu,Wei, Yin,Shi, Min
supporting information, p. 9282 - 9296 (2019/08/12)
A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.
Method for synthesizing ortho-amino aromatic ketone from aromatic carboxylic acid
-
Paragraph 0033; 0034, (2019/07/04)
Disclosed is a method for synthesizing ortho-amino aromatic ketone from aromatic carboxylic acid. The method comprises the steps that with 2-arylsulfonamido aromatic carboxylic acid shown in the description as a raw material and triphenylphosphine as a deoxidizer, under the illumination of blue light, in a 1,4-dioxane solution, under an argon atmosphere, in the presence of the dipotassium hydrogenphosphate, with [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as a photocatalyst, the ortho-amino aromatic ketone compound is obtained; the structure of the photocatalyst [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 is shown in thedescription.
Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information, p. 12724 - 12729 (2019/11/05)
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
Design, synthesis, crystal structures, and photophysical properties of tetraphenylethene-based quinoline derivatives
Zhu, Xiaolin,Wang, Danfeng,Huang, Hai,Zhang, Xueqiong,Wang, Shifan,Liu, Rui,Zhu, Hongjun
, (2019/07/09)
The incorporation of aggregation-induced emission (AIE) luminogens provides a molecule with enhanced fluorescent emission in the solid state. A representative AIEgen compound is tetraphenylethene (TPE). A series of new conjugates of quinolone derivatives with TPE units (1a - 1f) was synthesized and characterized. The influence on the photophysics of 1a - 1e with a variety of functional groups was investigated systematically by spectroscopic methods and simulated by density-functional theory calculations. A centrosymmetric compound donor-acceptor-donor-type compound 1f with two TPE moieties proved to be the most promising multifunctional material, it exhibited tri-colored (489–569 nm) fluorescence characteristics in tetrahydrofuran-H2O solution with a different water fraction and intense tri-colored solvatochromic (blue, green, and yellow) behaviors. These compounds could be applied as promising acid-base gas probe based on their evident color switch. Compounds 1a - 1f showed the advantage of being a potential piezochromic material.
Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives
Li, Peng-Hua,Yu, Liu-Zhu,Zhang, Xiao-Yu,Shi, Min
, p. 4516 - 4520 (2018/08/09)
A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.
