95644-00-1

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 614-16-4 Benzoylacetonitrile 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 128939-50-4 1,3,5-Triphenyl-7-thiophen-2-yl-2-thioxo-1,2,3,7-tetrahydro-pyrano[2,3-d]imidazole-6-carbonitrile 
• 113411-03-3 2-antipyrinyl-6-cyano-5-phenyl-7-(thien-2-yl)-4,7-dihydropyrazolo<1.5-a>pyrimidine 
• 1233127-10-0 5-(4-chlorophenyl)-2-phenyl-4-(thiophen-2-yl)furan-3-carbonitrile 
• 1378998-67-4 C₂₀H₁₉NO₂S 

Relevant academic research and scientific papers

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

Organocatalytic Asymmetric [4+2] Cycloaddition of 1-Acetylcyclopentene and 1-Acetylcyclohexene for the Synthesis of Fused Carbocycles

The first organocatalytic asymmetric [4+2]-cycloaddition reaction of 1-acetylcyclopentenes and 1-acetylcyclohexenes was developed. Enones having cyano groups were used as the dienophiles in this method. The reaction provides a useful practical route to th

Microwave synthesis of α-cyano chalcones

A novel methodology for facile production of α-cyano chalcones under microwave irradiation is described. Utilizing a Knoevenagel condensation between benzoylacetonitriles and aromatic aldehydes, substituted chalcones are generated via a 15-min, one-pot synthesis. Diversification of aromatic groups, including electron-withdrawing, electron-donating, and heterocyclic substitutions, has led to the isolation of over twenty colored, solid chalcone products. Furthermore the methodology can be extended to the synthesis of benzylidenemalononitriles as well as methyl and ethyl α-cyano cinnamates.

Tandem cross-Rauhut-Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

A novel tandem cross-Rauhut-Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies.

Replacement Substituent Constants for Simple Heterocycles

13C nmr absorptions are reported for the β-vinylic carbon atoms in 15 series of ethylenes bearing heterocyclic substituents.The data are used to establish the best single-parameter substituent constants, ?13, for the various heterocycles as replacements for para-substituted benzenes.Also reported are replacement dual substituent constants, including ?I and the various ?R scales needed in the Taft DSP treatment and those for F and R used in the Swain-Lupton treatment.Values of ?13, F, R, ?I, and ?Ro, respectively, for the various heterocycles as replacements for para-substituted benzenes are as follows: 2-furyl, -1.01 , 0.99, -2.51, 0.65, -0.60; 2-pyrryl, -2.53, 0.52, -5.09, -0.16, -0.62; 2-thienyl, -0.79, 2.49, -3.60, 1.82, -1.08; 3-thienyl, -0.40, 1.04, -1.57, 0.59, -0.39; 2-pyridyl, 0.88, 2.09, -0.24, 1.65, -0.45; 3-pyridyl, 0.60, 0.57, 0.63, 0.35, 0.04; and 4-pyridyl, 1.18, 1.22, 1.09, 0.92, -0.01.The DSP-NLR method of analysis is explored using electron demand parameters, ε, as determined for the vinylic side chains in para-substituted styrenes.

Activated Nitriles in Heterocyclic Synthesis: Synthesis of 6-Thiophen-2-yl and 6-Furan-2-ylthiazolopyridine Derivatives

A variety of new 6-thiophen-2-yl and 6-furan-2-ylthiazolopyridine derivatives could be prepared via the reaction of 2-functionally substituted methyl-2-thiazolin-4-one with cyanomethylenethiophen-2-yl and cyanomethylenefuran-2-yl derivatives.The st

α,β-Unsaturated Nitriles in Heterocyclic Synthesis: The Reaction of β-(2-Furanyl)- and β-(2-Thienyl)acrylonitrile with Active Methylene Reagents

The reactions of β-(2-furanyl)- and β-(2-thienyl)acrylonitrile with a variety of active methylene reagents are described.The investigations make several new pyran and pyranodiazole derivatives accessible.