912358-41-9

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 1449480-50-5 methyl 1-(4-bromophenyl)-5-(2-methoxyphenyl)-2-methyl-1H-pyrrole-3-carboxylate 
• 1396007-91-2 3-(4-bromo-phenyl)-5-methyl-3H-[1,2,3]triazole-4-carboxylic acid methyl ester 
• 1320232-49-2 C₂₀H₁₈BrNO₂ 

Relevant academic research and scientific papers

Citrus juice: Green and natural catalyst for the solvent-free silica supported synthesis of β-enaminones using grindstone technique

Aim and Objective: Citrus Juice as an efficient, cost-effective and green catalyst employed for one-pot synthesis of various β-substituted enaminones through the reaction of β-dicarbonyl compounds with different primary amines in a solvent-free conditions on silica gel as solid surface using grindstone technique in high yields and short reaction times. The presented procedure is operationally simple, practical and green. Material and Methods: The wide application of this procedure is demonstrated by the use of various substituted amines to react with β-dicarbonyl compounds. The method was successfully applied for primary amines (15 entries) and the related enaminones were well synthesized in good to excellent yields. Melting points were measured on an Electro thermal 9100 apparatus. 1HNMR and 13C NMR spectra were recorded on a FTNMR BRUKER DRX 500 Avence spectrometer. Chemical shifts were given in ppm from TMS as internal references and CDCl3 was used as the solvent as well. The IR spectra were recorded on a Perkin Elmer FT-IR GX instrument. The chemicals used in this work were purchased from Merck and Fluka chemical companies. Results: Grinding synthesis of citrus juice catalyzed enamination of 1,3-dicarbonyls (acetylacetone, methyl and ethyl-3-oxobutanoate) with various primary amines (aromatic and aliphatic) under solvent-free silica supported conditions was examined and studied (15 entries) and the obtained enaminones were well synthesized in good to excellent yields. Furthermore, the effect of various catalysts on the yield and reaction time for grinding synthesis of 3-phenylamino-but-2-enoic acid ethyl ester (1) by this method has evaluated as well. Conclusion: a novel, efficient and green protocol for the grinding synthesis of enaminones using citrus juice as natural catalyst has been presented. This methodology is user friendly, green and low cost procedure under mild reaction condition with faster reaction rates. The citrus juice is inexpensive and non-toxic which makes the process convenient, more economic and benign. Furthermore, applying grindstone technique in solvent-free conditions, use of silica gel as a solid and heterogeneous surface in reaction, high yields of products, cleaner reaction profiles, and availability of the reagents makes this method a better choice for synthetic chemists.

TBAI or KI-Promoted Oxidative Coupling of Enamines and N-Tosylhydrazine: An Unconventional Method toward 1,5- and 1,4,5-Substituted 1,2,3-Triazoles

A novel method for the synthesis of 1,5- and 1,4,5-substituted 1,2,3-triazoles has been reported. This approach is promoted by iodine-TBHP oxidation system using enamines and N-tosylhydrazine as materials, which avoid the dependence of traditional methods on azides and transition metals. Through this approach, various 1,5- and 1,4,5-substituted 1,2,3-triazoles were delivered in moderate to high yields. The mechanistic study indicated that an amino exchange would be involved in the reaction process. Moreover, the product methyl 1-(2-methoxyphenyl)-4-methyl-1H-1,2,3-triazole-5-carboxylate is a useful precursor to anti-influenza A agent, and further application research was conducted. (Figure presented.).

Oxidative cross-coupling/cyclization to build polysubstituted pyrroles from terminal alkynes and β-enamino esters

A novel silver-mediated highly selective synthesis of polysubstituted pyrroles by the C-H/C-H oxidative cross-coupling/cyclization of terminal alkynes with β-enamino esters has been developed. This protocol represents a simple, efficient and selective way to construct polysubstituted pyrroles in good yields from basic chemical materials.