2008
DOI: 10.1002/cjoc.200890196
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Synthesis of 14‐{[(Un)substituted phenyl] or alkyl}‐14H‐dibenzo[a,j]xanthenes Using Yb(OTf)3 as an Efficient Catalyst under Solvent‐free Conditions

Abstract: A series of 14-{[(Un)substituted phenyl] or alkyl}-14H-dibenzo[a,j]xanthenes were prepared under solvent-free conditions by Yb(OTf) 3 catalyzed condensation reactions of β-naphthol with various aldehydes. The process presented here is operationally simple, environmentally benign and has good to excellent yields. Furthermore, the catalyst can be recovered conveniently and reused efficiently.

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Cited by 10 publications
(5 citation statements)
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“…Xanthene derivatives can be prepared by several methods: cyclodehydration (Bekaert et al, 1992), the trapping of benzynes by phenols (Knight & Little, 2001), the palladium-catalysed cyclisation of polycyclic aryltriflate esters (Wang & Harvey, 2002), a simple and efficient procedure for the synthesis of xanthene derivatives through one-pot condensation of 2-naphthol with aryl aldehydes in the presence of niobium pentachloride (Bartolomeu et al, 2014), the condensation of cyclohexane-1,3-diones and aromatic aldehydes in the presence of solid acids (Karami et al, 2013a), amongst others (Horning & Horning, 1946;John et al, 2006;Saini et al, 2006;Zhang & Tao 2008;Zhang & Liu, 2008;Wang et al, 2008;Urinda et al, 2009;Lü et al, 2009;Maleki et al, 2011;Soleimani et al, 2011;Pramanik & Bhar, 2012;Dharma Rao et al, 2012;Karami et al, 2013bKarami et al, , 2013aKarami et al, , 2014Li et al, 2013;Cao et al, 2013;Shirini et al, 2013;Iniyavan et al, *Corresponding author, e-mail: lcsilva@fc.unesp.br 2014; Shirini et al, 2014Shirini et al, , 2015Preetam et al, 2015;Ilangovan et al, 2011). However, some of these methods involve long reaction times, extreme reaction conditions, expensive reagents and unsatisfactory yields, hence the improvement of these syntheses has been the target of several studies.…”
Section: Introductionmentioning
confidence: 99%
“…Xanthene derivatives can be prepared by several methods: cyclodehydration (Bekaert et al, 1992), the trapping of benzynes by phenols (Knight & Little, 2001), the palladium-catalysed cyclisation of polycyclic aryltriflate esters (Wang & Harvey, 2002), a simple and efficient procedure for the synthesis of xanthene derivatives through one-pot condensation of 2-naphthol with aryl aldehydes in the presence of niobium pentachloride (Bartolomeu et al, 2014), the condensation of cyclohexane-1,3-diones and aromatic aldehydes in the presence of solid acids (Karami et al, 2013a), amongst others (Horning & Horning, 1946;John et al, 2006;Saini et al, 2006;Zhang & Tao 2008;Zhang & Liu, 2008;Wang et al, 2008;Urinda et al, 2009;Lü et al, 2009;Maleki et al, 2011;Soleimani et al, 2011;Pramanik & Bhar, 2012;Dharma Rao et al, 2012;Karami et al, 2013bKarami et al, , 2013aKarami et al, , 2014Li et al, 2013;Cao et al, 2013;Shirini et al, 2013;Iniyavan et al, *Corresponding author, e-mail: lcsilva@fc.unesp.br 2014; Shirini et al, 2014Shirini et al, , 2015Preetam et al, 2015;Ilangovan et al, 2011). However, some of these methods involve long reaction times, extreme reaction conditions, expensive reagents and unsatisfactory yields, hence the improvement of these syntheses has been the target of several studies.…”
Section: Introductionmentioning
confidence: 99%
“…Yb(OTf) 3 proved to be an efficient catalyst for the same reaction under solvent-free conditions to yield a series of aryl-and alkyl-14H-dibenzo [a,j]xanthenes in good to excellent yields (Scheme 92, method B). 117 Both electronrich and electron-deficient benzaldehydes worked well, giving high yields of products; however, aliphatic aldehydes gave lower yields even after longer reaction times.…”
Section: Scheme 91 Yb(otf) 3 -Catalyzed Synthesis Of Coumarin-3-carbomentioning
confidence: 99%
“…Different catalysts such as sulfamic acid [10], p-TSA [11], selectfluor TM [12], iodine [13], silica sulfuric acid [14], Yb(OTf) 3 [15] and ionic liquids [16] were used in the synthesis of benzo[a]xanthenes derivatives. Moreover, the existing methods have not been conceded for the synthesis of tetrahydrobenzo[c]xanthene-8-ones from 1-naphthol because the electron density at 2-position of 1-naphthol is not sufficient for the formation of corresponding ortho-Quinone Methides (o-QMs).…”
Section: Introductionmentioning
confidence: 99%