64528-63-8

Upstream product

• 3282-30-2 pivaloyl chloride 
• 618-36-0 rac-methylbenzylamine 
• 1821-12-1 4-Phenylbutyric acid 
• 75-98-9 Trimethylacetic acid 
• 215657-43-5 N-pivaloyl-N-(2-fluorophenyl)methanesulfonamide 
• 754-10-9 2,2-dimethylpropionamide 
• 100-41-4 ethylbenzene 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 98-86-2 acetophenone 
• 1118-71-4 2,2,6,6-tetramethylheptane-3,5-dione 
• 300561-21-1 N-pivaloyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamide 
• 515863-57-7 N-(4,4-dimethyl-4,5-dihydro-thiazol-2-yl)-2,2,N-trimethyl-propionamide 

Downstream Products

• 64528-66-1 2,2-dimethyl-N-[1-phenylethyl]propanethioamide 
• 754-10-9 2,2-dimethylpropionamide 
• 91797-84-1 (R)-(+)-N-(1-phenylethyl)-2,2-dimethylpropanamide 
• 64528-62-7 (1S)-(+)-N-(2,2-dimethylpropionyl)-1-phenylethylamine 

Relevant academic research and scientific papers

An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines

We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.

Cleavage of 1,3-dicarbonyls through oxidative amidation

A mild and convenient protocol for the oxidative cleavage of 1,3-diketone compounds is described. Under metal-free conditions, the method converts the 1,3-dicarbonyls into amides when treated with (nBu4N)N3 and iodine in the presence of an amine at room temperature. Using this method, a range of 1,3-dicarbonyls with various structural motifs including sterically demanding substituents and ordinary functional groups were easily fragmented, and it is demonstrated that cyclic 1,3-dicarbonyls can be directly transformed into acyclic diamides through ring-opening. Initial mechanistic studies show that diazidation of the enol form is followed by nucleophilic substitution with the amine.

Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones

A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete

Transition Metal-Catalyzed C-H Amination Using Unactivated Amines

One aspect of the invention relates to a method of animation or amidation, comprising the step of combining a substrate, comprising a reactive C—H bond, and an amine or amide, comprising a reactive N—H bond, in the presence of an oxidizing agent and a metal-containing catalyst, thereby forming a product with a covalent bond between the carbon of the reactive C—H bond and the nitrogen of the reactive N—H bond.

NOVEL PYRIDINE OXIDE COMPOUND, AND PROCESS FOR PRODUCING CARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE CARBOXYLIC ACID DERIVATIVE WITH THE USE OF THE SAME

The invention relates to a pyridine oxide compound represented by formula (I), an optically active compound thereof, a salt thereof and a hydrate thereof, and, in the presence of the compound as a catalyst, performing 1) a method for producing an ester compound or an amide compound from a carboxylic acid equivalent and an alcohol or an amine, 2) an asymmetric esterification reaction or 3) an asymmetric amidation reaction. In formula (I), each R1 may be the same as the other R1 or different and each R1 represents an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom, a sulfur atom or a nitrogen atom; each R2 may be the same as the other R2 or different and each R2 represents a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom or the like, and R3 and R4 may be the same or different and R3 and R4 each represent a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom or the like.

Method for producing amides or esters

The invention relates to a method for producing amides or esters from carboxylic acids and from an amine constituent or alcohol constituent in the presence of a 1,3,5-triazine and optionally in the presence of an organic solvent and of a tertiary amine. According to the invention, a (bi)cyclic diamine or an adduct formed therefrom with the triazine constituent is used as a tertiary amine in a preferred stoichiometric ratio of diamine to the triazine constituent ranging from 0.30 to 1.10; the stoichiometric ratio of carboxylic acid to the amine constituent or alcohol constituent should range from 0.2 to 5.0, and; the molar ratio of carboxylic acid to the triazine constituent ranges from 0.5 to 1.5. Amino acids such as N-protected amino acids and peptides serve as carboxylic acid constituents and (C-protected) amino acids or a C-protected peptide serve as the amine constituent. 2-chlorine-4,6-dimethoxy-1,3,5-triazine (CDMT) is used as the preferred 1,3,5-triazine, and the N,N′-dimethyl-1,4-piperazine is used as the cyclic diamine. In addition to this method, which can be carried out at temperatures ranging from ?80 to +150 ° C. and in the presence of an organic solvent, the invention also relates to adducts comprised of (bi)cyclic diamine and 1,3,5-triazine. Compared to the prior art, higher yields with shorter reaction times are achieved using the described method, and distinctly smaller waste quantities of tertiary amine bases accrue.

N-Acyl-4,5-dihydro-4,4-dimethyl-N-methyl-2-thiazolamine as a chemoselective acylating agent

2-Methylamino-2-thiazoline reacted with alkyl acyl halides to produce N-acyl-2-methylamino-2-thiazolines, exo-acylated product regioselectively, which were found to be highly chemoselective acylating agents for primary amine in the presence of secondary amine and for the less sterically hindered of two different primary amines.

Studies on development of sufficiently chemoselective N-acylation reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides

A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd.

Metallic bismuth and aluminium: New and efficient catalysts for the preparation of various amides

A new and efficient method for the preparation of various amides has been achieved by a simple reaction of an acid chloride with primary and secondary amines in the presence of bismuth or aluminium powder in anhydrous toluene.

A versatile synthon for chemoselective N-acylation reagents, 2-fluoro-N-mesylaniline

2-Fluoro-N-mesylaniline 3b undergoes various N-acylalions easily to give 2-fluoro-N-acyl-N-mesylanilines 4b-8b, which function as good chemoselective N-acylation reagents, especially for benzyloxycarbonylation.