33768-43-3Relevant academic research and scientific papers
Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles
Larin, Egor M.,Lautens, Mark,Loup, Joachim
supporting information, p. 22345 - 22351 (2021/09/09)
A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.
Designing and Accurately Developing a [6 + 2] Dipolar Cycloaddition for the Synthesis of Benzodiazocines
Cai, Wei,Chen, Kaihong,He, Yanlin,Huang, You,Yu, Cui,Zhou, Yiming
, p. 5430 - 5434 (2021/07/26)
1,6-Dipolar cycloadditions represent a valuable strategy for the rapid construction of medium-sized rings. Herein, we describe the concept for the design of 1,6-dipoles that bypasses the regioselectivity. Through the introduction of an amino group into Morita-Baylis-Hillman (MBH) carbonates, unprecedented [6 + 2] dipolar cycloadditions were accurately developed with Cs2CO3, efficiently delivering a series of benzodiazocines in mild conditions. Computational studies bring a deeper understanding of this reaction.
Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
Schilling, Waldemar,Zhang, Yu,Riemer, Daniel,Das, Shoubhik
supporting information, p. 390 - 395 (2019/12/15)
Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.
Cp*Co(III)-Catalyzed o-Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Group Strategy
Dwivedi, Vikas,Khan, Bhuttu,Sundararaju, Basker
supporting information, (2020/01/25)
Transition metal-catalyzed ortho-selective C(sp2)?H amidation of weakly coordinating aldehydes remains limited to precious metals such as Ir, Rh, Ru, etc. Herein, we put forward a novel report on ortho-amidation of benzaldehydes employing user-
Synthesis method of O-aminobenzaldehyde compound
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Page/Page column 0029-0033, (2019/10/01)
The invention relates to a synthesis method of o-aminobenzaldehyde compounds, which takes benzaldehyde compounds as raw materials and oxazolone compounds to carry out activation reaction of benzaldehyde ortho-C-H bond to synthesize benzamide compounds und
Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
supporting information, p. 4703 - 4708 (2019/06/27)
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones
Ding, Jun,Jiang, Wei,Bai, He-Yuan,Ding, Tong-Mei,Gao, Dafang,Bao, Xiaoguang,Zhang, Shu-Yu
, p. 8889 - 8892 (2018/08/17)
An efficient and convenient ligand-free, rhodium-catalyzed ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones using H2O as the key promoter is described. Using this protocol, a wide range of benzaldehyde substrates were selectively amidated in good to excellent yields with broad functional group compatibility. KIE experiments revealed that the C-H bond activation was likely the rate-limiting step. In addition, computational studies indicated that the catalyst precursor interacted with water and dioxazolones to generate the active catalytic species. Notably, the practicality and efficacy of this method were illustrated by a late-stage amidation of an estrone-derived molecule and further transformations of the amidated product.
Rh-catalyzed Transient Directing Group Promoted C—H Amidation of Benzaldehydes Utilizing Dioxazolones
Wang, Xiaoyang,Song, Song,Jiao, Ning
supporting information, p. 213 - 216 (2018/01/27)
Transition-metal catalyzed C—H functionalization of benzaldehydes is of great interest in organic synthesis. Herein, we developed a transient directing group assisted amidation of benzaldehydes catalyzed by rhodium catalyst. With the employment of 10 mol% of 4-trifluoromethyl aniline, the in situ generated imine groups as the directing group efficiently enable this transformation. By using this protocol, a wide range of benzaldehydes were efficiently converted into the corresponding N-(2-formylphenyl)benzamides utilizing dioxazolones as the nitrogen source.
Rh(iii)-Catalyzed: Ortho -C-(sp2)-H amidation of ketones and aldehydes under synergistic ligand-accelerated catalysis
Hande, Akshay Ekanath,Ramesh, Vinay Bapu,Prabhu, Kandikere Ramaiah
supporting information, p. 12113 - 12116 (2018/11/21)
Rh(iii)-Catalyzed ortho-C-H amidation of ketones and aldehydes under cooperative metal organocatalysis has been utilized for synthesizing various ortho-amidocarbonyl analogs, and the reaction for the aldehyde proceeds at ambient temperature. The aniline derivative 3,5-bis(trifluoromethyl)aniline promotes the amidation reaction via a transient imine directing group. The efficient amidation agent is dioxazolone. The synthetic utility has been demonstrated in the synthesis of quindolinone alkaloids.
Pd/C-Catalyzed Aminocarbonylation of Aryl Iodides with Anthranils in Water Using Mo(CO)6 as the CO Source
Wang, Zechao,Yin, Zhiping,Wu, Xiao-Feng
supporting information, p. 15026 - 15029 (2017/10/18)
A convenient procedure for the synthesis of N-(2-carbonylaryl)benzamides has been developed. Through Pd/C-catalyzed aminocarbonylation of anthranils with various hindered and functionalized aryl iodides, the desired amides were afforded in moderate to good yields. The protocol is advantageous due to the recyclable Pd/C catalyst, safe Mo(CO)6 as the solid CO source, and environmentally benign water as solvent. No inert atmosphere protection is needed.
