163232-53-9Relevant academic research and scientific papers
L-Proline as an efficient catalyst for synthesis of N-heterocyclic chalcones as potential antibacterial agents
Bhupathi, Raja S.,Devi, B. Rama,Dubey
, p. 855 - 859 (2012/08/14)
The condensation of 4-hydroxy-3-acetyl-1H-quinoline-2-one 1 and substitutedbenzaldehydes 2a-i in DMSO solution at room temperature yields quinolone chalcone derivatives 3a-i. L-Proline has been found to be an efficient catalyst for this condensation between 1 and 2. Only 5 mol% of the catalyst is necessary to achieve good yields of the products. Reactions proceed smoothly with variations of the substituents. 1 itself is synthesized by the acylation of commercially available methyl anthranilate 4 with acetoacetic ester 5 in refluxing xylene and subsequent Dieckman intramolcular cyclization of the intermediary 2-methoxycarbonylanilide 6.
Solvent-free protocol for stereo selective crossed aldol condensation assisted by solid acid catalyst
Bhupathi, Raja S.,Rama Devi,Dubey
, p. 4215 - 4218 (2012/01/06)
A highly efficient, inexpensive, recyclable, green and solvent free protocol has been developed for crossed-aldol reaction. SiO2-OSO 3H has been found to be an efficient catalyst for the synthesis of 4-hydroxy-3-(3-phenyl-acryloyl)-1H-quinoline-2-one derivatives 3(a-i) from 4-hydroxy-3-acetyl-1H-quinoline-2-one (1) and substituted benzaldehydes 2(a-i). Reactions occurred smoothly with variations of the substituents. The reagent can be reused for five cycles with out sacrificing the yields and activity. This method is simple, convenient and the target compounds are produced in good to excellent yields. Compound 1 can be synthesized by the acylation of methyl anthranilate (4) with acetoacetic ester (5) in refluxing xylene and subsequent Dieckman cyclization of the intermediary 2-methoxycarbonyl anilide (6).
