18505-71-0

Upstream product

• 20357-25-9 6-nitroveratraldehyde 
• 106-49-0 p-toluidine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121-33-5 vanillin 

Downstream Products

• 350249-77-3 2-[(S)-1-hydroxy-3-phenylprop-2-yl]-2,3,4,5-tetrahydro-8,9-dimethoxyazepino[4,3-b]quinolin-1-one 
• 350249-75-1 ethyl 2-{[N((S)-1-hydroxy-3-phenyl)prop-2-yl]-3-aminopropyl}-6,7-dimethoxyquinoline-3-carboxylate 
• 597585-09-6 ethyl 6,7-dimethoxy-2-phenyl-3-quinolinecarboxylate 

Relevant academic research and scientific papers

A novel traceless solid-phase Friedlaender synthesis

(Matrix presented) A new solid-phase synthesis of quinolines based on a Friedlaender-type reaction between the resin-bound azomethine 1b and ketones 2 is described. This cyclative cleavage approach affords quinolines 3a-f in 50-81% yields. The polymer-bou

Toward new camptothecins. Part 6: Synthesis of crucial ketones and their use in Friedl?nder reaction

In the context of the preparation of camptothecin and luotonin A analogs, the synthesis of some key keto-precursors and their use in Friedl?nder condensation are described. This paper also focuses on the stability of these keto intermediates and emphasizes the major differences between indolizinones and pyrroloquinazolinones series. Noteworthy is also the report of some original structures isolated as by-products of some experiments.

Synthesis and bioevaluation of 22-hydroxyacuminatine analogs

A series of 22-hydroxyacuminatine analogs was prepared by using different Friedlaender condensations. Several of the new compounds were tested for antiproliferative activity on cancer cell lines and for topoisomerase I inhibitory activity.

Stable annelated chiral NADH models with a rigidified amide part in the quinoline series: Synthesis, reactivity and grafting on a Merrifield resin

The synthesis of new chiral nicotinamide adenine dinucleotide hydrogenated models derived from quinoline is described. Using a biomimetic approach, the out-of-plane positioning of the amide carbonyl was obtained by involving the chiral auxiliary in a lactam structure. It is shown that electron-donating groups on the benzene ring of the quinoline structure are necessary to obtain high chemical yields during the reduction of methyl benzoylformate. An interesting variation of the enantioselectivity as a function of magnesium ion concentration has been observed. Under the best conditions, methyl mandelate was obtained in up to 95% ee (R). To facilitate the recycling of these models, grafting of reagent 4 on a Merrifield resin has been developed. The resulting polymer-supported reagent 4 was tested in the asymmetric reduction of methyl benzoylformate.