Vapour-phase synthesis of 2-methyl- and 4-methylquinoline over BEA zeolites

Brosius, Roald; Gammon, David W.; Laar, Frederik van; Steen, Eric van; Sels, Bert F.; Jacobs, Pierre

doi:10.1016/j.jcat.2006.02.015

Cited by 28 publications

(24 citation statements)

References 24 publications

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“…Solids such as Al 2 O 3 [6], H 2 SO 4 / SiO 2 [7][8][9], NaHSO 4 /SiO 2 [10,11], HClO 4 /SiO 2 [12], silica gel-supported phosphomolybdic acid [13], KAl (SO 4 ) 2 Á12H 2 O/SiO 2 [14], sulfonated cellulose [15] and silica-propylsulfonic acid [16] have been reported as heterogeneous catalysts for Friedländer condensation [17]. In addition, synthesis of quinolines starting from aniline and different aldehydes catalyzed by H-BEA, under vapour phase conditions, has been reported [18]. More recently, we reported on mesoporous materials as novel and efficient catalysts for the condensation between 2-aminoaryl ketones and ethyl acetoacetate via Friedländer reaction selectively leading to the corresponding quinolin-2(1H)-ones [19].…”

Section: Introductionmentioning

confidence: 99%

Zeolites Promoting Quinoline Synthesis via Friedländer Reaction

et al. 2010

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Catalytic performance of zeolites H-BEA, H-MFI, H-FAU and H-MOR, exhibiting textural differences and with different Brønsted and Lewis acid sites concentration, have been studied in the synthesis of quinolines via Friedländer reaction. H-BEA and H-FAU efficiently promoted the condensation of 2-aminoaryl ketones 3 with ethyl acetoacetate (4a) or acetylacetone (4b) under mild reaction conditions, those being the first examples of zeolites as catalysts for this transformation. While H-FAUshowed similar catalytic behaviour than that reported for (Al)SBA-15 affording mixtures of quinolines 5 and quinolones 6, H-BEA mainly led to quinolines 5 in almost total selectivity and good yields. However, H-MFI and H-MOR zeolites afforded quinolones 6 as the major reaction product. Methodology reported here was found to be useful for the synthesis of biologically active compounds with excellent yields avoiding unnecessary purifications protocols and tedious work-up procedures.

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Section: Introductionmentioning

confidence: 99%

Zeolites Promoting Quinoline Synthesis via Friedländer Reaction

et al. 2010

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“…Several methods have been reported for the synthesis of quinolines, such as Dobner 7 , Skraup 8 , Pfitzinger and Friedlander 9,10 . But, among them, Friedlander reaction is the most simple and straightforward method.…”

Section: Introductionmentioning

confidence: 99%

Silica-based sulfonic acid (MCM-41-SO3H): a practical and efficient catalyst for the synthesis of highly substituted quinolines under solvent-free conditions at ambient temperature

Maleki¹,

Javanshir²,

Sharifi³

2014

10.5267/j.ccl

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In this work, a variety of highly substituted quinolines were readily synthesized via Friedlander annulation using Brönsted acid silica-based sulfonic acid as a modified catalyst under solventfree conditions at room temperature. This efficient procedure has the advantages of giving the target compounds in high yields, short reaction times, simple workup procedure, reusability of the catalyst, and environmentally benign conditions.

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“…Since the discovery of penicillin, the development of novel synthetic or natural molecules with highly specific antibacterial properties has attracted great interest [6,7] in which context, oxo-quinolines have been the focus of attention [8][9][10]. To overcome the problem of the development of bacterial resistance to antibacterial compounds, novel quinolones with specific properties have been developed [11][12][13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%