1161433-07-3

Upstream product

• 40204-26-0 malonic acid monobenzyl ester 
• 62-53-3 aniline 
• 261639-91-2 5-[(hydroxy)(phenylamino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 100-51-6 benzyl alcohol 
• 201230-82-2 carbon monoxide 
• 52267-51-3 benzyl diazoacetate 

Downstream Products

• 15580-32-2 malonanilic acid 

Relevant academic research and scientific papers

Carbene radicals in cobalt(II)-porphyrin-catalysed carbene carbonylation reactions; A catalytic approach to ketenes

One-pot radicals: Cobalt(III)-carbene radicals, generated by metallo-radical activation of diazo compounds and N-tosylhydrazone sodium salts with cobalt(II) complexes of porphyrins, readily undergo radical addition to carbon monoxide, allowing the catalytic production of ketenes. These ketenes subsequently react with various amines, alcohols and imines in one-pot tandem transformations to produce differently substituted amides, esters and β-lactams in good isolated yields. Copyright

TMSCL as a rate-accelerating additive in acylations of amines with 5-(α-AMINO-α′-Hydroxy)methylene meldrum acids

Aspects are presented of the acylation of amines, alcohols, and thiols with 5-(α-amino-α′-hydroxy)methylene Meldrum acids. We placed special emphasis on the acylation reaction of secondary amines with 5-(α-amino-α′-hydroxy)methylene Meldrum acids, which, because of their basicity, caused problems concerning salt formation with a Meldrum acid derivative. We found that secondary amines, which react at the slowest rate and give a poor yield with 5-(α-amino-α′-hydroxy)methylene Meldrum's acid, react quickly and with high yields with the same reagent in the presence 1 to 3 equivalents of TMSCl. Acylation with this derivative of Meldrum acid was optimized for such factors as reaction temperature, solvent polarity, and acidity of the environment. We have prepared a wide range of nonsymmetrical malononic acid diamids, esters, and thioesters of malonamic acid. Taylor & Francis Group, LLC.

Pd-catalyzed carbonylation of diazo compounds at atmospheric pressure: A catalytic approach to ketenes

The carbonylation of carbenes through catalytic cycles is highly desirable due to the importance of ketene-mediated reactions in organic synthesis. In this investigation, a highly efficient and mild catalytic approach toward ketene intermediates has been developed based on Pd-catalyzed carbonylation of diazo compounds with CO. When α-diazocarbonyl compounds or N-tosylhydrazone salts are heated in the presence of a palladium catalyst under atmospheric pressure of CO, ketene intermediates are formed in situ, where they undergo further reactions with various nucleophiles such as alcohols, amines, or imines. The Pd-catalyzed tandem carbonylation-Staudinger cycloaddition gives β-lactam derivatives in good yields with excellent trans diastereoselectivity. The results from DFT calculation on the reaction mechanism suggest that Pd is involved in the [2 + 2] cycloaddition process and affects the diastereoselectivity of the β-lactam products by assisting isomerization of the addition intermediate. On the other hand, the acylketenes generated from the Pd-catalyzed carbonylation of α-diazoketones react with imines in a formal [4 + 2] cycloaddition manner to afford 1,3-dioxin-4-one derivatives. This straightforward carbonylation provides a new approach toward highly efficient catalytic generation of ketene species under mild conditions.

Design and synthesis of bis-amide and hydrazide-containing derivatives of malonic acid as potential HIV-1 integrase inhibitors

HIV-1 integrase (IN) is an attractive and validated target for the development of novel therapeutics against AIDS. In the search for new IN inhibitors, we designed and synthesized three series of bis-amide and hydrazide-containing derivatives of malonic acid. We performed a docking study to investigate the potential interactions of the title compounds with essential amino acids on the IN active site.