7324-84-7Relevant academic research and scientific papers
Regio- and stereoselective 1,3-dipolar cycloaddition reactions of C-aryl (or hetaryl)-N-phenylnitrones to monosubstituted ylidene malononitriles and 4-benzylidene-2-phenyloxazol-5(4H)-one
Mekheimer, Ramadan A.,Al-Zaydi, Khadijah,Ibrahim, Mahmoud A. A.,Al-Shamary, Asma,Sadek, Kamal
, p. 317 - 326 (2017)
The first example of 1,3-dipolar cycloaddition reactions of C-aryl (or hetaryl)-N-phenylnitrones to monosubstituted ylidene malononitriles and 4-benzylidene-2-phenyl-oxazol-5(4H)-one is described. The reaction of C-(4-(dimethylamino)phenyl)-N-phenyl-nitro
Chitosan as a biodegradable heterogeneous catalyst for Knoevenagel condensation between benzaldehydes and cyanoacetamide
Anbu, Nagaraj,Maheswari, Raju,Elamathi, Vimali,Varalakshmi, Perumal,Dhakshinamoorthy, Amarajothi
, (2020/03/03)
A natural biopolymer chitosan is being employed as heterogeneous solid base catalyst for the Knoevenagel condensation reaction between benzaldehydes and cyanoacetamide under mild reaction conditions. This reaction offers the direct synthesis of condensati
Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)
Rupanawar, Bapurao D.,Veetil, Sruthi M.,Suryavanshi, Gurunath
, p. 6232 - 6239 (2019/11/05)
Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.
Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
Liu, Yingtian,Dang, Xinxin,He, Yu,Bai, Hudong,Chen, Xuehong,Li, Jun-Long,Fan, Junting,Jiang, Hezhong,Li, Jiahong
, p. 662 - 671 (2019/02/20)
A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit
Aqueous-Phase Synthesis and Solid-Phase Fluorescence of 3-(Methoxyphenyl)-2-cyanoacrylamides
Bezgin,Ershov,Ievlev, M. Yu.,Belikov, M. Yu.,Bardasov
, p. 1100 - 1102 (2018/09/12)
Reactions of methoxybenzaldehydes with cyanoacetamide in water in the presence of cocamidopropylamine oxide afforded 84–94% of 3-(methoxyphenyl)-2-cyanoacrylamide which showed solid-phase fluorescence with the emission maxima located at λ 421–469 nm.
Montmorillonite-KSF mediated one step synthesis of pyranochromene derivatives
Subbareddy, Chitreddy V.,Subashini, Radhakrishnan,Sumathi, Shanmugam
, p. 747 - 754 (2018/06/26)
One-pot three-component reaction of substituted aromatic aldehydes, 2-cyanoacetamide and 4-hydroxycoumarin in the presence of Montmorillonite-KSF (MKSF) in ethanol results in the formation of pyrano[3,2-c]chromene-3-carboxylates (5a-m) has been described. The reaction was tested in different alcohols, afforded pyrano [3,2-c] chromene-3-carboxylates (5a-m) of the corresponding alcohols in good yield. The mechanism reveals that the alcohol (as solvent) plays a major role in the inter conversion of amide to the corresponding esters with Montmorillonite KSF (M-KSF) as a catalyst. Excellent yields, inexpensive and readily available substrates, environmentally benign reaction condition, shorter reaction time, and easy workup are the major advantageous features of this protocol.
Triflic acid-catalyzed metal-free synthesis of (: E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones
Rupanwar, Bapurao D.,Chavan, Santosh S.,Shelke, Anil M.,Suryavanshi, Gurunath M.
supporting information, p. 6433 - 6440 (2018/04/23)
A TfOH-catalyzed highly efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64-94% yields under metal-free conditions. The reaction proceeds through sequential Knoevenagel condens
An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction
Narendar Reddy, Thatikonda,Raktani, Bikshapathi,Perla, Ramesh,Ravinder, Mettu,Vaidya, Jayathirtha Rao,Babu, N. Jagadeesh
, p. 9203 - 9209 (2017/08/29)
Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.
Cascade Synthesis of 2-Cyanoacrylamides through Deacetalization and/or Knoevenagel Condensation followed by Selective Monohydration of Acetals and Aldehydes over Solid Acid Ferrites
Kamble, Sumit B.,Rode, Chandrashekhar V.
, p. 2678 - 2687 (2016/08/30)
A new protocol of cascade synthesis for biologically active 2-cyanoacrylamides (1) was developed. The reaction proceeds over a novel magnetically retrievable solid-acid composite of iron oxide, poly(vinylpyrrolidone) and phosphotungstic acid (Fe3O4/PVP–PWA) in AcOH–H2O medium under reflux conditions. This transformation is facilitated through single-site Br?nsted acid catalyzed cascade reactions involving deacetalization and/or Knoevenagel condensation followed by selective monohydration of nitriles starting from acetals (5) and aldehydes (2) with malononitrile (3). A series of aldehydes, dimethyl and diethyl acetals, along with some heterocyclic aldehydes were successfully transformed to 2-cyanoacrylamides with >95 % yields. TEM images confirmed the coating of the PVP over nanosized Fe3O4. Stereoselective monohydration of 2-benzylidenemalononitriles (4) to E isomers was demonstrated by NOESY experiments. The catalyst could be efficiently recycled seven times on employment of both acetals and aldehydes as substrates, as a result of its magnetic nature.
(E)-2-Cyano-3-(substituted phenyl)acrylamide analogs as potent inhibitors of tyrosinase: A linear β-phenyl-α,β-unsaturated carbonyl scaffold
Son, Sujin,Kim, Haewon,Yun, Hwi Young,Kim, Do Hyun,Ullah, Sultan,Kim, Seong Jin,Kim, Yeon-Jeong,Kim, Min-Soo,Yoo, Jin-Wook,Chun, Pusoon,Moon, Hyung Ryong
, p. 7728 - 7734 (2015/12/20)
In this study, we synthesized (E)-2-cyano-3-(substituted phenyl)acrylamide (CPA) derivatives which possess a linear β-phenyl-α,β-unsaturated carbonyl scaffold and examined their inhibitory activities against tyrosinase. CPA analogs exerted inhibitory acti
