76263-66-6

Upstream product

• 901-90-6 7-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4-one 
• 100-52-7 benzaldehyde 
• 43192-31-0 2-bromo-4-methoxybenzaldehyde 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 622-58-2 p-Tolylisocyanate 
• 75227-26-8 3-[(3-Methoxy-phenyl)-(toluene-4-sulfonyl)-amino]-propionic acid ethyl ester 
• 412337-55-4 3-[(3-Methoxy-phenyl)-(toluene-4-sulfonyl)-amino]-propionyl chloride 
• 75227-24-6 ethyl 3-(3-methoxyphenylamino)propionate 
• 76263-71-3 N-(3-methoxy-phenyl)-N-(toluene-4-sulfonyl)-β-alanine 
• 536-90-3 m-Anisidine 

Downstream Products

• 76263-69-9 1-[(3S,3aR)-7-Methoxy-3-phenyl-5-(toluene-4-sulfonyl)-3,3a,4,5-tetrahydro-pyrazolo[4,3-c]quinolin-2-yl]-ethanone 
• 103688-15-9 C₂₄H₂₁NO₅S 
• 103688-19-3 7-Methoxy-2,3-diphenyl-5-(toluene-4-sulfonyl)-4,5-dihydro-2H-pyrazolo[4,3-c]quinoline 

Relevant academic research and scientific papers

Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones

The synthesis of 3-alkyliden-2,3-dihydro-4-quinolones has been accomplished in a domino fashion through a three-step sequence that comprised an initial aza-Baylis-Hillman reaction, followed by a 1,3-rearrangement and an intramolecular amination. Starting from readily available aryl vinyl ketones and N-tosyl imines, the reaction with PPh3, CsOAc and CuI in CH3CN gave rise, in good overall yields, to final 3-alkyliden-4-quinolone derivatives, valuable scaffolds in medicinal chemistry. The simultaneous addition of two bases, PPh3 and CsOAc, was found to be crucial for the success of the process. While PPh3 promoted the reversible aza-Baylis-Hillman reaction, CsOAc triggered the subsequent 1,3-rearrangement, which shifted the initial equilibrium and allowed to complete the synthetic sequence upon the addition of CuI. (Figure presented.).

Studies in Antifertility Agents: Part XXVII - Synthesis of 2-Acetyl-3-aryl-5-tosyl-7/8-H (or methoxy)-3,3a,4,5-tetrahydropyrazoloquinolines

N-Tosyl-2,3-dihydro-4-quinolones (12-14), prepared from aniline, m- and p-anisidines by reported procedures, on condensation with araldehydes in the presence of NaOMe give the corresponding 3-arylidene-4-quinolones (15-18).Refluxing of 15-18 with NH2-NH2*H2O in gl.AcOH affords the title compounds, 2-acetyl-3-aryl-5-tosyl-7/8-H (or methoxy)-3,3a,4,5-tetrahydropyrazoloquinolines (19-22).The stereochemistry of the title compounds based on the assignments of C3-H, C3a-H, C4-H2 protons has been studied by PMR decoupling experiments.In preliminary screening, compounds 19 and 22 have been found to prevent pregnancy at 20 mg/kg dose in female albino rats, but are ineffective at lower doses.None of the compounds tested shows any significant pharmacological activity.