2006
DOI: 10.1039/b514635f
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Molecular iodine: a highly efficient catalyst in the synthesis of quinolinesvia Friedländer annulation

Abstract: A mild and efficient route for the synthesis of quinolines and polycyclic quinolines via Friedländer annulation, utilizing molecular iodine (1 mol%) as a new catalyst, is described.

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Cited by 167 publications
(47 citation statements)
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References 68 publications
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“…It should be noted that molecular iodine as catalyst for effecting various organic transformations [27] has lately drawn considerable attention. In our case, the absence of iodomethyleneoxazoline [28] excludes an iodocyclization mechanism.…”
Section: Resultsmentioning
confidence: 99%
“…It should be noted that molecular iodine as catalyst for effecting various organic transformations [27] has lately drawn considerable attention. In our case, the absence of iodomethyleneoxazoline [28] excludes an iodocyclization mechanism.…”
Section: Resultsmentioning
confidence: 99%
“…Recently, a concise and practical one-pot synthesis of quinazolones from anthranilic acid, ortho esters and amines promoted by Yb(OTf) 3 , 3 La(NO 3 ) 3 •6H 2 O or p-toluenesulfonic acid, 4 SiO 2 -FeCl 3 , 5 Ye(III)-resin 6 and NaHSO 4 •SiO 2 or amberlyst-15 7 has been reported. In recent years, the use of molecular iodine as a cheap and easily available catalyst has received considerable attention for various organic transformations 8 such as synthesis of decahydroquinolinones, 9 dihydroperoxidation of ketones, 10 synthesis of quinolines, 11 synthesis of Cbz-protected β-amino ketones, 12 imino Diels-Alder reaction 13 and cross-aldol condenation.…”
Section: Introductionmentioning
confidence: 99%
“…introduced gold catalysed quinoline synthesis under microwave-assisted conditions. Lewis acids (Hu et al, 2003;McNaughton & Miller, 2003;Zhang & Wu, 2007), Bronsted acids (Muscia et al, 2006), molecular iodine (Wu et al, 2006), proline (Jiang et al, 2008), ionic liquids (Dabiri et al, 2008) and transition metals (Martinez et al, 2007;Gabriele et al, 2007;Vieira &Alper, 2007;Cho & Ren, 2007) were some of the catalysts involved in different synthetic protocols for quinoline structural motif. However many of the aforementioned reactions require strong acids or bases, toxic flammable organic solvents, or hazardous/ expensive catalysts and elevated temperatures.…”
Section: Quinoline Derivativesmentioning
confidence: 99%