88991-46-2

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 495-69-2 Hippuric Acid 
• 98-88-4 benzoyl chloride 
• 109547-80-0 C₂₇H₂₄NO₂PS 

Downstream Products

• 88991-36-0 Methyl (E)-2-benzoylamino-3-(3-thienyl)-propenoate 
• 89103-25-3 (E)-2-Benzoylamino-3-(3-thienyl)-2-propenoic acid 
• 113505-89-8 cis-3-benzamido-3-carbomethoxy-4-(3-thienyl)-Δ¹-pyrazoline 
• 89921-39-1 (R)-N-benzoyl-3-(3-thienyl)-alanine 
• 22574-47-6 D-2-amino-3-thiophen-3-yl-propionic acid 
• 88991-22-4 (Z)-2-Benzoylamino-3-(3-thienyl)-2-propenoic acid 
• 88991-47-3 (E)-2-Phenyl-5-oxo-4-(3-thienylmethylene)-4,5-dihydro-1,3-oxazole 

Relevant academic research and scientific papers

[Et3NH][HSO4]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones

A facile, green and stereoselective approach for the synthesis of azlactones/oxazolones 3(a-q) has been developed. The protocol involves reaction of hippuric acid and substituted heterocyclic/aromatic aldehydes in ionic liquid [Et3NH][HSO4] to yield the desired 4-arylidene-2-phenyl-5(4H)-oxazolones in excellent yields (94-97%) with a high degree of purity. The remarkable feature of this pathway is that the ionic liquid eliminates the use of toxic and expensive acetic anhydride and is endowed with catalytic and medium engineering ability. This eco-friendly approach improved synthetic efficiency (94-97% yield), minimizing the production of chemical waste without using highly toxic reagents for the synthesis and more notably, it promoted the selectivity for Z-azlactones/oxazolones. Density functional theory (DFT) calculations revealed that the Z-isomer of compound 3a is stabilised by 2.32 kcal mol-1 more than the E-isomer. This synthetic scheme possesses diverse applicability and is compatible to a range of functional groups (electron donating/electron withdrawing).

UNUSUAL AMINO ACIDS. IV. ASYMMETRIC SYNTHESIS OF THIENYLALANINES

(Z)-2-N-Acylamino-3-thienyl-acrylic acids and thei esters were prepared by known procedures and hydrogenated to the corresponding optically active 2-N-acetyl(or benzoyl)-3-(2- or 3-thienyl)-alanines with optically yields up to 90percent using the rhodium complexes of 'PROPRAPHOS" 6a,b and O,N-bis(diphenylphosphino)-2-exo-hydroxy,3-endo-methylamino-norbornane 6c as chiral catalysts.Recrystallization and deacylation of the obtained amino acid derivatives yields the optically pure hydrochlorides of the thienylalanines as the free amino acids.

IMINOPHOSPHORANE-MEDIATED SYNTHESIS OF 4-HETEROARYLMETHYLENE-2-ARYL-2-OXAZOLIN-5-ONES.

A number of 2-oxazolin-5-one derivatives have been prepared by reaction of iminophosphoranes 1 with aroyl chlorides.