7391-40-4

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C5H8N2O/c1-7(2)5(8)3-4-6/h3H2,1-2H3

Upstream product

• 124-40-3 dimethyl amine 
• 105-56-6 ethyl 2-cyanoacetate 
• 28112-07-4 1-Cyano-2-dimethylaminoethin 
• 105-34-0 methyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 77-78-1 dimethyl sulfate 
• 107-91-5 cyanoacetic acid amide 
• 1585-74-6 dimethylchloroamine 
• 15029-36-4 N-ethylcyanoacetamide 
• 16130-58-8 cyanoacetic acid chloride 
• 131297-22-8 5-(Dimethylamino-isopropylamino-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 75-31-0 isopropylamine 
• 131297-18-2 5-(tert-Butylamino-methylsulfanyl-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 

Downstream Products

• 1857-18-7 3-amino-N,N-dimethyl-propionamide 
• 34644-27-4 2-dimethylamino-2-ethoxy-1-cyanoethylene 
• 15430-62-3 N,N-dimethyl-2-bromo-3-nitrilopropionamide 
• 103409-20-7 2-Amino-7-phenyl-[1,8]naphthyridine-3-carboxylic acid dimethylamide 
• 846023-30-1 3,4-dimethoxyanilino-N-(dimethyl)-2-cyano-2-propenamide 
• 1018452-62-4 C₁₂H₁₃N₃OS 
• 1018452-63-5 C₁₃H₁₅N₃O₂S 
• 1354724-72-3 (R)-N-(1-(4-cyano-5-(dimethylamino)thiophen-2-yl)heptyl)-4-methylbenzenesulfonamide 
• 146561-43-5 2-cyano-N,N-dimethylethanethioamide 
• 55804-68-7 coumarin 337 

Relevant academic research and scientific papers

Synthesis and Docking Study of Novel Pyranocoumarin Derivatives

Abstract: A new series of fused tricyclic coumarin derivatives were designed, synthesized by a simple and convenient method, starting from 4-hydroxycoumarin and virtually screened by molecular docking on the target protein 3FRZ (PDB ID: 3FRZ), a HCV RNA-dependent RNA polymerase, for potency against hepatitis C virus (HCV). Efficient binding to the target protein was found for most of the synthesized compounds.

Cobalt-Catalyzed Allylic Alkylation Enabled by Organophotoredox Catalysis

Co-catalyzed allylic substitution reactions have received little attention, arguably because of the lack of any known advantage of Co catalysis over either Rh or Ir catalysis. Described here is a general and regioselective Co-catalyzed allylic alkylation using an in situ catalyst activation by organophotoredox catalysis. This noble-metal-free catalytic system exhibits unprecedentedly high reactivities and regioselectivities for the allylation with an allyl sulfone, for the first time, representing the unique synthetic utility of the Co-catalyzed method compared to the related Rh- and Ir-catalyzed reactions.

Preparation method for N,N-dimethylcyanoacetamide

The invention discloses a preparation method for N,N-dimethylcyanoacetamide (DMCA). The method is characterized by comprising the following steps: (1) adding a dimethylamine aqueous solution into methyl cyanoacetate dropwise under the temperature of -15 to 0 DEG C, and performing a reaction under stirring for 1-2h; (2) enabling the temperature to return to a room temperature, continuing a reactionunder stirring for 2-3h, then adding toluene, and performing heating refluxing; and raising the temperature to 35 DEG C, performing a reaction for 20-30min, raising the temperature again to 42 DEG C,performing a reaction for 10min, and performing natural cooling to the room temperature; (3) performing a microwave reaction for 10min, then performing ultrasonic dispersion for 30-40min, performingnatural cooling to the room temperature; (4) allowing the obtained material to stand for 2-3h under the temperature of -5 DEG C for precipitating a solid; and (5) performing vacuum filtration, performing vacuum drying on the obtained solid. The method disclosed by the invention omits a reflux water separation process, greatly reduces the amount of waste water, makes the post-treatment process simplified and has the advantage of environmental protection; and the DMCA product obtained by the process has a white appearance, the purity reaches 99% or more, and the yield is 92.5%.

Direct synthesis of polysubstituted 2-aminothiophenes by Cu(ii)-catalyzed addition/oxidative cyclization of alkynoates with thioamides

A facile and direct synthetic method was developed for the construction of structurally important 2-aminothiophenes in moderate to excellent yields (up to 91%), via Cu(ii)-catalyzed addition/oxidative cyclization of readily available thioamides with alkynoates under an air atmosphere. This journal is

Optically active thiophenes via an organocatalytic one-pot methodology

A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.

Synthesis of new 8-formyl-4-methyl-7-hydroxy coumarin derivatives

8-Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives were synthesized via Penchem condensation followed by Duffs reaction. Treatment of this with N,N-di substituted cyano acetamides in the presence of piperdine afforded New 8- Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives (7a-o). Their structures were characterized by IR, 1H and 13C NMR and Mass spectral and elemental analysis data.

Synthesis and insecticidal activities of novel neonicotinoid analogs bearing an amide moiety

Figure represented. A series of novel neonicotinoid analogs containing an amide moiety were synthesized, characterized, and subsequently evaluated for their insecticidal activity. According to the preliminary bioassay, the compounds 6c, 6e, 6f, 6j, 6n, and 6r exhibited > 50% activity against Nilaparvata lugens at 100 mg/L. Amongst the active compounds, 6f and 6r revealed insecticidal activities similar to that displayed by standard buprofezin. J. Heterocyclic Chem., (2011)

Enols of substituted cyanomalonamides

(Chemical Equation Presented) Twenty open-chain mono-, di-, and trialkyl and aryl-N-substituted cyanomalonamides R2R1NCOCH-(CN) CONHR3 were prepared. In solution, signals for both amide and a single enol are mostly observed, despite the potential for E and Z isomeric enols. The equilibrium (KEnol) values between the amides and the enols were determined in different solvents by NMR spectra. They decrease on increasing the polarity of the solvent in the order CDCl3 ～ C6D6 > THF-d8 (CD3)2CO > CD3CN > DMF-d7 > DMSO-d6. For the R1R2NCOCH(CN)CONHR3 system when R1 = R2 = H, Me or R1 = H, R2 = Me, K Enol for R3 follows the order: C6F5 > Ph ≥ An ≥ i-Pr ≥ t-Bu, and for R1, R2:H, H > Me, H > Me, Me in all solvents. A unique feature is the appreciable % enol in DMSO-d6 when R1 = R2 = H, in contrast with enol systems with other electron-withdrawing groups (EWGs). Calculations (B3LYP/6-31G**) corroborate the higher KEnol values for less alkyl-substituted systems, showing that in the most stable conformer when R1 = H, R2 = R3 = Me the N-hydrogens are closer to the CN group. The order of promoting substituents for enol of amide formation is CONH2 > CO2CH2CF3 > CO2Me > CONHMe. The solid-state structures of the isolated species, determined by X-ray crystallography, were either amides or enols, and a higher KEnol(CDCl3) value does not ensure a solid enol structure. In no system were both solid species isolated. The X-ray structures of the enols were temperature-dependent. In most cases, the difference between the O-H and O...H bond lengths at low temperature were appreciable, but they become closer at the higher temperature. Similar tendency for either the C=C/C-C or the C-O/C=O bonds was observed. This is ascribed to a hydrogen shift between two regioisomeric enols in an asymmetric double-well potential, which becomes faster at a higher temperature. Calculations show that the enol structures are nonsymmetrical, resembling the lower temperature structures, even when they are chemically symmetrical, but the energy differences between the two regioisomers are 1 kcal. The hydrogen bonds in the enol moiety are strong, with O...O distances 2.45 A, and are resonance-assisted hydrogen bonds. IR spectra in solution and the solid state qualitatively corroborate the NMR and X-ray structure determination.

Cyanoketene and Iminopropadienones

Cyanoketene (8) is generated in high yields on flash vacuum thermolysis (FVT) of suitably substituted Meldrum's acid derivatives (5-[(alkylamino)(methylthio or alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones) (3e-j), and also on FVT of cyanoacetic acid derivatives 9e,f,g,j,k,m. The major reaction pathway from 3 proceeds via ketenimines 6 and (alkylimino)propadienones 7, the latter undergoing a retro-ene reaction to 8. A minor pathway is via imidoylketenes 4e,h and oxoketenimines 5e,h, which undergo retro-ene reactions to 9. All intermediates were characterized by Ar matrix FTIR and tandem mass spectrometry (collisional activation MS). Trapping of 4, 5, and 8 with nucleophiles is also reported. The preference of 1,3-X shifts over 1,5-H shifts in imidoylketenes 12 (X = SMe or NMe2) is corroborated by the calculated activation barriers. Neat cyanoketene is highly reactive, reacting at or below 80 K, and this is attributed to the availability of a low-lying ketene LUMO. The IR spectrum of cyanoketene (Ar, 14 K) is dominated by two absorptions at 2163 (s; C=C=O) and 2239 (w; CN) cm-1 in excellent agreement with density functional (B3-LYP/6-31G*) and ab initio (QCISD/6-31G*) calculations.