74084-23-4

Upstream product

• 32997-17-4 (5Z)-2-(4-methylphenyl)-5-(phenylmethylidene)-3,5-dihydro-4H-imidazol-4-one 
• 150-30-1 Phenylalanine 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 59490-37-8 (S)-methyl (4-methylbenzoyl)phenylalaninate 
• 1236384-36-3 C₁₇H₁₅NO₂ 

Relevant academic research and scientific papers

Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols

A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an efficient and mild access to chiral dihydrocoumarins bearing adjacent tertiary and quaternary stereogenic centers in high yields with excellent diastereo- and enantioselectivities.

Organocatalyzed asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones: Synthesis of α,α-disubstituted α-amino acid derivatives

The first asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones catalyzed by cinchona alkaloid derived bifunctional thiourea catalysts was developed. A series of α,α-disubstituted α-amino acid derivatives bearing a quaternary stereocenter at the α-position were obtained in high yields with excellent diastereo- and enantioselectivities (up to -20:1 dr and 99% ee). In addition, the trichloromethyl moiety in these adducts was identified as a good leaving group.

Potassium channel openers

Compounds of formula I: are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.

Potassium channel openers

Compounds of formula I: are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.

Synthesis of Acylamino Acids and Acylamino Acid Amides by Simultaneous Reduction and Hydrolysis of Unsaturated 2,4-Disubstituted 2-Imidazolin-5-ones

Twelve acylamino acids (II) and two acylamino acid amides (III) have been prepared by the simultaneous reduction and hydrolysis of unsaturated 2,4-disubstituted 2-imidazolin-5-ones (I) with a mixture of zinc dust and potassium hydroxide solution.

Synthesis of Acylamino Acid Amides and Acylamino Acids via 2,4-Disubstituted 2-Imidazolin-5-ones

Unsaturated 2,4-disubstituted 2-imidazolin-5-ones (I) have been reduced with a mixture of hydriodic acid and red phosphorus in the presence of acetic anhydride to give the saturated 2,4-disubstituted 2-imidazolin-5-ones (II) which have been hydrolysed to acylamino acid amides (III) and acylamino acids (IV) with sodium hydroxide solution under different conditions.In all six acylamino acid amides (23 - 51percent yields) and four acylamino acids (26 - 65percent yields) have been prepared.One saturated 2-imidazolin-5-one, namely 2-phenyl-4-benzyl-2-imidazolin-5-one has been isolated from the reaction in 40percent yield and identified.