24512-96-7

Upstream product

• 64-17-5 ethanol 
• 6367-36-8 tert-butyl 2-azidoacetate 
• 100-52-7 benzaldehyde 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 4192-77-2 ethyl cinnamate 
• 62355-67-3 ethyl (+/-)-(2R,3R)-2-bromo-3-hydroxy-3-phenylpropanoate 
• 4540-33-4 piperdinium acetate 
• 188475-18-5 ethyl 4-azido-2-diazo-3-oxobutanoate 
• 637-81-0 ethyl-2-azidoacetate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 73579-75-6 (Z)-3-Phenyl-2-(triethoxy-λ⁵-phosphanylideneamino)-acrylic acid ethyl ester 
• 73579-80-3 (Z)-2-(Diethoxy-phosphorylamino)-3-phenyl-acrylic acid ethyl ester 
• 73579-95-0 C₂₃H₂₂NO₃P 
• 1621105-98-3 ethyl 4-phenyl-3-(p-tolyl)isoxazole-5-carboxylate 
• 16565-48-3 ethyl 3,4-diphenylisoxazole-5-carboxylate 
• 1621105-99-4 ethyl 3-(4-methoxyphenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-00-0 ethyl 3-(4-nitrophenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-01-1 ethyl 3-(4-fluorophenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-02-2 ethyl 3-(4-chlorophenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-03-3 ethyl 3-(3-chlorophenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-04-4 ethyl 3-(2-chlorophenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-05-5 ethyl 3-(2-bromophenyl)-4-phenylisoxazole-5-carboxylate 
• 1621106-06-6 ethyl 3-(4-bromophenyl)-4-phenylisoxazole-5-carboxylate 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Visible-Light-Mediated Synthesis of Pyrazines from Vinyl Azides Utilizing a Photocascade Process

A convenient method for the synthesis of substituted pyrazines from vinyl azides has been developed. This method is enabled by a dual-energy and electron-transfer strategy by visible-light photocatalysis. Initially, vinyl azides are activated by a triplet sensitization process from an excited ruthenium photocatalyst in the presence of water to form dihydropyrazines, followed by a single-electron-transfer (SET) process under oxygen (air) atmosphere that leads to the tetrasubstituted pyrazines in good to excellent yields.

An efficient synthesis of double 2-alkylthio-5-phenylmethylidene-4H- imidazol-4-ones

Double 2-alkylthio-5-phenylmethylidene-4H-imidazol-4-ones 6 were synthesized by S-alkylation of double 2-thioxo-5-phenylmethylidene-4- imidazolidinone 5, which was obtained via cyclization of vinyl isothiocyanate 4 with ethylenediamine.

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Method for synthesising azidophenylethyl acrylate

The invention discloses a method for synthesising (Z)-2-azido-3-phenylethyl acrylate. The method comprises the following steps: adding 1.6g of sodium wires into a 500mL round-bottom flask containing 120-160ml of absolute ethyl alcohol, and stirring on a magnetic stirrer to achieve complete dissolution; accurately weighing 40mmol of benzaldehyde and 120mmol of alkenylethyl azidoacetate, adding the benzaldehyde and alkenylethyl azidoacetate in a 100mL conical flask, adding 80-100mL of absolute ethyl alcohol, uniformly mixing the benzaldehyde, alkenylethyl azidoacetate and absolute ethyl alcohol, and then adding the mixed solution into a constant-pressure dropping funnel; stirring at -25 DEG C, and dropping the mixed solution of benzaldehyde and alkenylethyl azidoacetate in a sodium ethoxide solution drop by drop under nitrogen protection; after the dropping is finished, heating the reaction system to -10 DEG C, and reacting for 8-26h under the nitrogen protection; after the reaction is complete, carrying out a quenching reaction by virtue of 40ml of saturated ammonium chloride solution; and adding 10-30mL of water in the system, extracting 3*10mL of the solution by virtue of ethyl acetate, washing an organic phase by virtue of 50mL of saturated sodium chloride solution, then adding anhydrous magnesium sulphate in the organic phase for water removal drying, and finally carrying out reduced pressure distillation for solvent removal, thus obtaining the oily product azidophenylethyl acrylate.

Synthesis of 3,4,5-trisubstituted isoxazoles by the 1,3-dipolar cycloaddition reaction of α-azido acrylates and aromatic oximes

A novel, one-pot, cascade reaction sequence featuring the 1,3-dipolar cycloaddition reaction of α-azido acrylates and aromatic oximes was developed. This procedure provides an efficient, straightforward and metal-free method for the synthesis of 3,4,5-trisubstituted isoxazoles under mild reaction conditions.

Indoles via Knoevenagel-Hemetsberger reaction sequence

A series of substituted indoles have been synthesized by the sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and coupled 1H-13C NMR analysis of the ethyl α-azido-β-arylacrylates indicate that the condensation is stereospecific - only the Z-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted ethyl α-azido-β- arylacrylates resulted in the formation of both the 5- and 7- substituted indoles - the 5-regioisomer being slightly favored over the 7-regioisomer. Analogous thermal treatment of (2Z, 2Z′)-diethyl 3,3′-(1,3- phenylene)bis(2-azidoacrylate) and (2Z, 2Z′)-diethyl 3,3′-(1,4- phenylene)bis(2-azidoacrylate) exclusively produced pyrroloindoles, diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, respectively. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification.

Design, synthesis and aromatase inhibitory activities of novel indole-imidazole derivatives

A series of novel indole-imidazole derivatives have been prepared and evaluated in vitro on the aromatase inhibitory activities. The results suggested that proton or a small electron-withdrawing group at para-position of the phenyl ring would enhance the inhibitory activities and any bulky group should be avoided in order to keep a relative small volume for this kind of molecules.

One-pot three-component approach to the synthesis of polyfunctional pyrazoles

A simple, multicomponent, and straightforward reaction of vinyl azide, aldehyde, and tosylhydrazine affords the construction of 3,4,5-trisubstituted 1H-pyrazoles regioselectively in the presence of base with moderate to excellent yields. A range of functionality could be tolerated in this methodology, and a possible mechanism is proposed.

Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds

(Chemical Equation Presented) Two synthetic methods for tetra- and trisubstituted N-H pyrroles are presented: (i) the thermal pyrrole formation by the reaction of vinyl azides with 1,3-dicarbonyl compounds via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides; (ii) the Cu(II)-catalyzed synthesis of pyrroles from α-ethoxycarbonyl vinyl azides and ethyl acetoacetate through the 1,4-addition reaction of the acetoacetate to the vinyl azides. By applying these two methods, regioisomeric pyrroles can be prepared selectively starting from the same vinyl azides.

Synthesis, proton and 13C NMR and reaction mechanism studies of novel isoindolones derivatives, obtained through TAWERS procedure

A series of novel isoindolone derivatives (13-18) were prepared in goods yields by applying the TAWERS methodology. A general approach for formation of isoindolones from the aza-Wittig reaction of iminophosphoranes with dialdehydes under neutral and mild conditions was realized. Using 1D NMR a [1,3]-hydride migration was detected. The assignment of the structures and conformation behavior of the derivatives was achieved using 1D and 2D NMR (NOESY, DEPT, HMQC, and HMBC).