36192-61-7Relevant academic research and scientific papers
Dual Role of Anthranils as Amination and Transient Directing Group Sources: Synthesis of 2-Acyl Acridines
Kim, Saegun,Han, Sang Hoon,Mishra, Neeraj Kumar,Chun, Rina,Jung, Young Hoon,Kim, Hyung Sik,Park, Jung Su,Kim, In Su
, p. 4010 - 4014 (2018)
The transient directing group promoted C(sp2)-H functionalization of benzaldehydes with anthranils by a cationic rhodium(III) catalyst is described. Notably, anthranils have been used as both transient directing groups and amination sources to afford 2-acyl acridines through direct C-H amination followed by acid-mediated cyclization. A range of substrate scopes and functional group tolerance were observed.
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 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
supporting information, p. 7540 - 7544 (2021/10/12)
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes
Li, Quanzhe,Liu, Jiaxin,Shi, Min,Wei, Yin
, (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.
Novel 2-acyl Acridine derivatives, preparation method thereof, and pharmaceutical compositions for the prevention or treatment of cancer containing the same as an active ingredient
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Paragraph 0050; 0155; 0167; 0168, (2020/04/24)
The present invention relates to a novel 2-acyl acridine derivative having an anticancer activity and an anti-inflammatory activity, a preparation method thereof, and a pharmaceutical composition comprising the same as an active ingredient. The novel 2-acyl acridine derivative is a 2-acyl acridine derivative represented by chemical formula 1, an isomer of the 2-acyl acridine derivative, or a pharmaceutically acceptable salt of the 2-acyl acridine derivative. As results of taking keenly to the study of 2-acyl acridine to use 2-acyl acridine in treatment of various viruses, cancer, leukemia and others, the present inventors have found that a 2-acyl acridine derivative can be efficiently produced by intramolecular cyclization in addition to C-H amination due to catalyzation of aldimine and rhodium (III) along with anthranyl, and the 2-acyl acridine derivative produced through such a process has an excellent effect of treating cancer and inflammation. Therefore, it is expected that the 2-acyl acridine derivative can be used as a pharmaceutical composition for prevention or treatment of cancer or inflammation. Further, it is expected that a preparation method of the 2-acyl acridine derivative using a rhodium (III) catalyst, as a reaction which can be applied to or introduced into a wide range of functional groups and has regioselectivity and chemical selectivity, is very useful in the synthesis of a new drug or a compound having biological activities.COPYRIGHT KIPO 2020
Asymmetric Transfer Hydrogenation of o-Hydroxyphenyl Ketones: Utilizing Directing Effects That Optimize the Asymmetric Synthesis of Challenging Alcohols
Clarkson, Guy J.,Wills, Martin,Zheng, Ye
supporting information, (2020/05/05)
A systematic range of o-hydroxyphenyl ketones were reduced under asymmetric transfer hydrogenation conditions using the C3-tethered catalyst 2. Two directing effects, i.e., an o-hydroxyphenyl coupled to a bulky aromatic on the opposite side of the ketone substrate, combine in a matched manner to deliver reduction products with very high enantiomeric excess.
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
, 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.
Lewis or Br?nsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif
Wei, Hao-Zhao,Yu, Liu-Zhu,Shi, Min
, p. 135 - 139 (2019/12/26)
We developed a facile synthetic method to access cyclopenta[b]naphthalene derivatives via the Lewis or Br?nsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.
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
, 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.
