58265-44-4

Upstream product

• 3242-56-6 2-diazocyclohexanone 
• 100-46-9 benzylamine 
• 953077-10-6 cyclopentyl-imidazol-1-yl-methanone 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 3400-45-1 cyclopentanecarboxylic acid 
• 51671-45-5 3-benzyl-3,4,5,6,7,7a-hexahydro-benzo[1,2,3]triazol-3a-ol 

Relevant academic research and scientific papers

Amide Synthesis via Aminolysis of Ester or Acid with an Intracellular Lipase

A unique lipase (SpL) from Sphingomonas sp. HXN-200 was discovered as the first intracellular enzyme for the aminolysis of ester or acid to produce amide. Reactions of a series of esters and amines with SpL gave the corresponding amides 3a-g in high yield with high activity. SpL also showed high enantioselectivity and high activity for enantioselective ester aminolysis, producing amides (R)-3h-j in high ee from the corresponding racemic ester or amine. Moreover, SpL was found to be highly active for the aminolysis of carboxylic acid, which was generally considered infeasible with the known aminolysis enzymes. The aminolysis of several carboxylic acids afforded the corresponding amides 3a, 3d, 3k, 3l, and 3n in good yield. The intracellular SpL was expressed in Escherichia coli cells to give an efficient whole-cell biocatalyst for amide synthesis. Remarkably, high catalytic activity was observed in the presence of water at 2-4% (v/v) for free enzyme and 16% (v/v) for whole cells, respectively. Accordingly, E. coli (SpL) wet cells were used as easily available and practical catalysts for the aminolysis of ester or acid, producing a group of useful and valuable amides in high concentration (up to 103 mM) and high yield. The newly discovered intracellular SpL with unique properties is a promising catalyst for green and efficient synthesis of amides.

Nickel-Catalyzed Esterification of Aliphatic Amides

Recent studies have demonstrated that amides can be used in nickel-catalyzed reactions that lead to cleavage of the amide C?N bond, with formation of a C?C or C?heteroatom bond. However, the general scope of these methodologies has been restricted to amides where the carbonyl is directly attached to an arene or heteroarene. We now report the nickel-catalyzed esterification of amides derived from aliphatic carboxylic acids. The transformation requires only a slight excess of the alcohol nucleophile and is tolerant of heterocycles, substrates with epimerizable stereocenters, and sterically congested coupling partners. Moreover, a series of amide competition experiments establish selectivity principles that will aid future synthetic design. These studies overcome a critical limitation of current Ni-catalyzed amide couplings and are expected to further stimulate the use of amides as synthetic building blocks in C?N bond cleavage processes.

Amide formation in one pot from carboxylic acids and amines via carboxyl and sulfinyl mixed anhydrides

An efficient method has been developed for the preparation of yet unknown acyclic mixed anhydrides of carboxylic and sulfinic acids. Sterically hindered 2-methylbut-3-ene-2-sulfinyl carboxylates add primary and secondary amines preferentially onto the carbonyl moieties realizing a new method for the one-pot preparation of carboxamides. It uses 1:1 mixtures of carboxylic acids and amines without a base, requires no excess of reagents, and liberates only volatile coproducts. Protected di- and tripeptides have been prepared in solution without epimerization by application of this method.

Mild decarboxylative activation of malonic acid derivatives by 1,1′-carbonyldiimidazole

Chemical equations presented. Malonic acid derivatives undergo unusually mild decarboxylation when treated with N,N′-carbonyldiimidazole (CDI) at room temperature to generate the carbonyl imidazole moiety in high yield, which can be reacted further with a variety of nucleophiles in an efficient one-pot process.

New derivatives of benzylamide with anticonvulsant activity

Previously obtained picolinic acid benzylamide is a potent anticonvulsant with low neurotoxicity. In search for new effective anticonvulsants twelve new benzylamides (1-12) were synthesized and preliminary evaluated in the Anticonvulsant Screening Program (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH. Two of them appeared the most promising: 1- cyclopentenecarboxylic acid benzylamide (1- Cpc-BZA) (9) showed MES ED 50 = 85,36 mg/kg (PI = 2,49), scPTZ ED50 = 1,37 mg/kg (PI = 1,37), 6Hz-EST ED50 = 50,29 mg/kg and cyclopentanecarboxylic acid benzylamide (Cpc-BZA) (11) showed pilocarpine ED50 = 154.75 mg/kg and pilocarpine ED97 = 270.95 mg/kg.

Microwave specific Wolff rearrangement of α-diazoketones and its relevance to the nonthermal and thermal effect

α-Diazoketones possess high electric dipole moments, as a consequence of the dipolar nature of the diazocarbonyl functional group. The vectorial analysis, theoretical calculations (PM3 and ab initio), and literature reports based on experimental and theor