52906-62-4Relevant academic research and scientific papers
Catalyst-Free [3 + 3] Annulation/Oxidation of Cyclic Amidines with Activated Olefins: When the Substrate Olefin Is Also an Oxidant
Han, Wendan,Li, Yuanhang,Raveendra Babu, Kaki,Li, Jing,Tang, Yuhai,Wu, Yong,Xu, Silong
, p. 7832 - 7841 (2021/06/25)
Herein we describe a catalyst-free regioselective [3 + 3] annulation/oxidation reaction of cyclic amidines such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) and DBN (1,5-diazabicyclo(4.3.0)non-5-ene) with activated olefins, i.e., 2-arylidenemalononitriles and 2-cyano-3-aryl acrylates, to afford tricyclic 2-pyridones and pyridin-2(1H)-imines, respectively. The mechanism has been proposed based on DFT calculations. In the reaction, the cyclic amidines serve as C,N-bisnucleophiles for the cyclization, while the olefins play a dual role by acting as both reactants and oxidants.
Asymmetric Reaction of p-Quinone Diimide: Organocatalyzed Michael Addition of α-Cyanoacetates
Reddy, Sivakumar N.,Reddy, Venkatram R.,Dinda, Shrabani,Nanubolu, Jagadeesh Babu,Chandra, Rajesh
supporting information, p. 2572 - 2575 (2018/05/17)
Hitherto unknown catalytic enantioselective transformation of p-quinone diimides is achieved using chiral bifunctional organic molecules. Bifunctional thiourea compounds catalyze the Michael addition of cyanoacetates with excellent yields and enantioselec
Solvent-free preparation method for substituted cyanoacetate compound
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Paragraph 0027; 0033-0035, (2018/02/04)
The invention discloses a solvent-free preparation method for a substituted cyanoacetate compound. The method is characterized by comprising the following steps: subjecting an aldehyde compound (I) represented by a formula shown in the description, cyanoacetate (II) represented by a formula shown in the description and a dihydropyridine ester (III) represented by a formula shown in the description to a hybrid reaction under solvent-free conditions, and carrying out separation and purification after the reaction is completed, thereby obtaining the substituted cyanoacetate (IV) represented by a formula shown in the description. According to the method, aldehydes, cyanoacetate and dihydropyridine esters serve as raw materials for the first time, and the substituted cyanoacetate can be efficiently synthesized through a one-pot method reaction without solvents and catalysts, so that the preparation method is simple, efficient and environmentally friendly.
A substituted cyano acetate preparation method (by machine translation)
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Paragraph 0022-0039; 0044, (2017/05/19)
The invention discloses a substituted cyano acetate preparation method, characterized in that comprises the following steps: (I) takes the aldehyde class compound, cyano acetic acid esters (II) and (III) dihydro pyridine ester, uses water as solvent, mixe
Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; Unexpected reductions and vinylogations
Harisha, Attimogae Shivamurthy,Nayak, Suresh Parameshwar,Nagarajan, Kuppuswamy,Row, Tayur Narasingarow Guru,Hosamani, Amar A.
, p. 2880 - 2889 (2016/05/24)
Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined. The study was extended to cyclic molecules incorporating such systems like thiazolidinedione 8, 3-cyanocoumarin 9 and 4-arylidene-isoquinoline-2,4-diones 11. The last group gave vinylogated products, 4-cinnamylidene-isoquinolinediones and 4-hydroxylated species. A few examples of arylidene derivatives from malononitrile, ethyl acetoacetate, acetyl acetone and ethyl methylsufonylacetate were investigated. Ethyl cinnamate and β-nitrostyrene were unaffected. The reaction is considered to be possibly radical mediated, since addition of free radical quencher suppressed the reaction. Contrary to the effects of thermal conditions, irradiation of 1f in ethanol at 254 and 365 nm gave complex mixtures. A few other interesting observations in this study are noted: vinylogation of 1f with acetaldehyde to 3f; formation of 3f from 1f by the treatment with triethylamine, palladium carbon and reduction of 1f to 2f by triethylammonium formate in DMF.
Base-Promoted Cascade Approach for the Preparation of Reduced Knoevenagel Adducts Using Hantzsch Esters as Reducing Agent in Water
He, Tao,Shi, Ronghua,Gong, Yimou,Jiang, Guangyou,Liu, Ming,Qian, Shan,Wang, Zhouyu
supporting information, p. 1864 - 1869 (2016/07/16)
A cascade Knoevenagel condensation-reduction approach, which was carried out in water, has been reported. Using Hantzsch esters as reducing agent, under the promotion of base, a variety of reduced Knoevenagel adducts could be easily prepared by direct alkylation of malononitrile, ethyl 2-cyanoacetate, and 2-(4-nitrophenyl)acetonitrile, respectively. Meanwhile, a gram-scale synthesis of the protocol was also realized with excellent isolated yield.
Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives - Demethylation, reduction and vinylogation
Harisha, Attimogae Shivamurthy,Nayak, Suresh Parameshwar,Nagarajan, Kuppuswamy,Guru Row, Tayur Narasingarow,Hosamani, Amar A.
, p. 1427 - 1431 (2015/03/04)
3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also.
Overturning established chemoselectivities: Selective reduction of arenes over malonates and cyanoacetates by photoactivated organic electron donors
Doni, Eswararao,Mondal, Bhaskar,O'Sullivan, Steven,Tuttle, Tell,Murphy, John A.
supporting information, p. 10934 - 10937 (2013/08/23)
The prevalence of metal-based reducing reagents, including metals, metal complexes, and metal salts, has produced an empirical order of reactivity that governs our approach to chemical synthesis. However, this reactivity may be influenced by stabilization of transition states, intermediates, and products through substrate-metal bonding. This article reports that in the absence of such stabilizing interactions, established chemoselectivities can be overthrown. Thus, photoactivation of the recently developed neutral organic superelectron donor 5 selectively reduces alkyl-substituted benzene rings in the presence of activated esters and nitriles, in direct contrast to metal-based reductions, opening a new perspective on reactivity. The altered outcomes arising from the organic electron donors are attributed to selective interactions between the neutral organic donors and the arene rings of the substrates.
Nanocrystalline ZnO for Knoevenagel condensation and reduction of the carbon, carbon double bond in conjugated alkenes
Hosseini-Sarvari, Mona,Sharghi, Hashem,Etemad, Samane
scheme or table, p. 715 - 724 (2009/02/07)
A novel efficient and eco-friendly nanocrystalline ZnO catalyst was used for the Knoevenagel condensation and for the reduction of C=C double bonds at room temperature in the absence of solvents.
Unprecedented reaction between ethyl α-cyanocinnamate and o-phenylenediamine: Development of an efficient method for the transfer hydrogenation of electronically depleted olefins
Kumar, Satish,Kapoor, Kamal K.
, p. 2809 - 2814 (2008/02/13)
A reaction between ethyl α-cyanocinnamate and o-phenylenediamine under thermal conditions yielded 2-cyano-3-phenyl-propionic acid ethyl ester, 2-phenyl benzimidazole, and ethyl cyanoacetate. The mechanistic revelations led to the development of a simple and efficient transfer-hydrogenation process from the in situ generated benzimidazolines to activated olefins under solventless and catalyst-free conditions. Georg Thieme Verlag Stuttgart.
