68259-66-5

Upstream product

• 100-46-9 benzylamine 
• 103808-45-3 (S)-N-benzyl-2-hydroxypropionamide 
• 87605-11-6 propynoic acid benzylamide 
• 127-17-3 2-oxo-propionic acid 
• 123-54-6 acetylacetone 

Relevant academic research and scientific papers

Synthesis of 1,2,5-thiadiazole-3(2H)-thiones and 1,2,5-thiadiazol-3(2H)-ones from 1,2,3-dithiazoles

5H-1,2,3-Dithiazole-5-thiones and 5H-1,2,3-dithiazol-5-ones undergo a new transformation into 1,2,5-thiadiazole-3(2H)-thiones and 1,2,5-thiadiazol-3(2H)-ones, respectively, upon treatment with primary amines; the structure of thiadiazolethione was confirm

Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature

A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede

Selective amidation by a photocatalyzed umpolung reaction

A metal-catalyzed organic transformation merged with another organophotocatalyst has been developed under mild conditions for production of α-ketoamides. CuI-catalyzed highly selective and rapid COCH2-amidation in the presence of electrophilic CαO bonds, which is synchronized by an eosin Y (EY)-photocatalyst, furnishes a wide range of labile α-ketoamides, unsymmetrical oxalamides and chiral analogues on the treatment of 1,3-dicarbonyls with amines, PhIO and LED light at room temperature. The current strategy opens up a new avenue to making photocatalysis a common synthetic tool for large-scale production in academia and industry.

Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides

The treatment of 5H-1,2,3-dithiazole-5-thiones 1 in chloroform under reflux and 5H-1,2,3-dithiazol-5-ones 2 in THF at room temperature with primary aliphatic amines and benzylamine afforded 1,2,5-thiadiazole-3(2H)-thiones 3 and 1,2,5-thiadiazol-3(2H)-ones 6, respectively. The structure of dithiazolone 3f was confirmed by X-ray diffraction analysis. The reaction of dithiazolone 2e bearing an electron-donating methyl group in the 4-position gave 2-oxoacetamide 7e in high yield. The reaction of thiones 1 with secondary aliphatic amines in DMSO yielded 2-iminothioacetamides 8 in moderate yields together with elemental sulfur. Interestingly, the treatment of dithiazolones 2 with secondary amines under the same conditions afforded 2-oxoacetamides 9-the products of the hydrolysis of corresponding imino derivatives 10, which was isolated as 10b. A general mechanism was proposed for the formation of the products.

HETEROCYCLIC MODULATORS OF THE GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-κB ACTIVITY AND USE THEREOF

Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including obesity, diabetes, inflammatory and immune diseases, and have the structure of Formula (I) or stereoisomers or prodrugs or solvates or pharmaceutically acceptable salts thereof, wherein A, B, J, K, Z, R, Ra, Rb, Rc, and Rd, are defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising said compounds.

Tricyclic modulators of the glucocorticoid receptor, AP-1, and/or NF-kB activity and use thereof

Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including obesity, diabetes, inflammatory and immune diseases, and have the structure of formula (I) or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein B, J, K, Z, R, Ra, Rb, Rc, Rd, Rq, Rw, m and n are defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising said compounds.

Acetylenic Amides. 2. The Generation and Reactions of Dianions Derived From 2-Propynamides

The dianion of N-benzyl-2-propynamide can be generated by the treatment of 4 with two equivalents of LDA at -65 deg C or ethylmagnesium bromide at -20 deg C.The trilithio species 6 is readily formed using 3 equivalents of LDA.Reaction of 5 with aldehydes or ketones produce hydroxypropynamides 9 in good yields.Silation of 5a with chlorotrimethylsilane produces N-benzyl-3-trimethylsilyl-2-propynamide (13) in high yield.Reduction of 9 furnishes either fully saturated amides 15 or partially reduced cis-olefins 16 or 18.Compounds 16, on heating, rearrange to 4-ketoamides 17.Carboxylation of 5a with carbon dioxide produces 3-benzyl-2,4-dioxo-5-oxazidinylacetic acid (11).Warming 11 in dimethyl sulfoxide results in the loss of carbon dioxide and the formation of N-benzylpyruvamide (21).