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ChemInform Abstract: Silica Sulfuric Acid: A Simple, Efficient, and Reusable Heterogeneous Catalyst for the One-Pot Synthesis of Aryl-14H-dibenzo[a,j]xanthenes under Conventional Heating and Solvent-Free Conditions

Chemistry of Heterocyclic Compounds (Impact Factor: 0.62). 02/2008; 44(2):143-147. DOI: 10.1007/s10593-008-0035-3

ABSTRACT

A novel approach towards the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes is described from a known reaction between
substituted aldehydes and β-naphthol in the presence of heterogeneous catalyst silica sulfuric acid under conventional heating
as well as solvent-free conditions to afford good to excellent yields. The catalyst is reusable; it can be used several times
without any decrease in the product yield.

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    • "M.p./ • C Product R Time/h Yield a /% Found Reported b VIa C 6 H 5 48 90 190 190–191 (Ding et al., 2007) VIb 4-FC 6 H 4 48 91 247 245 (Poupelin et al., 1978a) VIc 3-FC 6 H 4 48 93 222 220 (Poupelin et al., 1978a) VId 2-FC 6 H 4 24 95 233 234 (Poupelin et al., 1978a) VIe 4-ClC 6 H 4 48 95 295 295 (Rostamizadeh et al., 2008) VIf 3-ClC 6 H 4 48 96 200 199–200 (Kumari et al., 2008) VIg 2-ClC 6 H 4 24 96 220 221 (Poupelin et al., 1978a) VIh 4-BrC 6 H 4 48 97 300 300–302 (Jin et al., 2006) VIi 3-BrC 6 H 4 48 97 195 194–195 (Rostamizadeh et al., 2008) VIj 2-BrC 6 H 4 24 96 215 216–217 (Nasr-Esfahani & Abdizadeh, 2013) VIk 4-OCH 3 C 6 H 4 48 70 201 202–203 (Gong et al., 2009) VIl 3-OCH 3 C 6 H 4 24 91 182 180–181 (Bhattacharya & Rana, 2007) Vim 2-OCH 3 C 6 H 4 24 93 261 258–259 (Mirjalili et al., 2011) VIn 4-NO 2 C 6 H 4 24 98 329 326–328 (Tabatabaeian et al., 2011) VIo 3-NO 2 C 6 H 4 24 97 225 224–226 (Ding et al., 2007) VIp 4-CH 3 C 6 H 4 24 95 233 233–234 (Rostamizadeh et al., 2008) VIq 3-CH 3 C 6 H 4 24 96 201 197–198 (Mirjalili et al., 2011) VIr 2-CH 3 C 6 H 4 24 98 208 208 (Poupelin et al., 1978a) VIs 4-[(CH 3 ) 3 C]C 6 H 4 24 92 302 303 (Prasad & Nath, 2012) VIt 4-C 6 H 5 C 6 H 4 48 96 285 281 (Poupelin et al., 1978b) VIu 4-SCH 3 C 6 H 4 48 88 213 216 (Hunnur et al., 2008) "
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    ABSTRACT: A simple and efficient procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives through one-pot condensation of 2-naphthol with aryl aldehydes in the presence of niobium pentachloride is described. The reactions were carried out using 25 mole % of NbCl5, at ambient temperature, and in acceptable reaction times, affording excellent yields of the products.
    Full-text · Article · Nov 2014 · Chemical Papers- Slovak Academy of Sciences
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    • "There are several methods reported in literatures for the synthesis of xanthene derivatives including the reaction of aryloxy magnesium halides with triethyl orthoformate (Casiraghi et al., 1973), cyclodehydration (Bekaert et al., 1992), trapping of benzynes by phenols (Knight and Little, 2001), intermolecular phenyl carbonyl coupling reactions of benzaldehydes and acetophenones (Kuo and Fang, 2001), cyclization of polycyclic aryl triflate esters (Wang and Harvey, 2002) and cyclocondensation between 2-hydroxy aromatic aldehydes and 2-tetralone (Jha and Beal, 2004). Although, the preparation of xanthenes has been achieved via the reaction of various aldehydes and 2- naphthols by cyclodehydration in the presence of diverse catalysts, such as AcOH–H 2 SO 4 (Sarma and Baruah, 2005), p-TSA (Khosropour et al., 2005), MeSO 3 H (Bhattacharya and Rana, 2007), sulfamic acid-ionic liquid (Wu et al., 2009), iodine (Das et al., 2006; Fei-Qing et al., 2007), heteropoly acid (Mohammadpour et al., 2007), silica sulfuric acid (FischerHunnur et al., 2008), amberlyst-15 (Ko and Yao, 2006), cyanuric chloride (Bigdeli et al., 2007), LiBr (Saini et al., 2006), CoPy 2 Cl 2 (Madhav et al., 2008), Yb(OTf) 3 (Su et al., 2008), Sc[N(SO 2 C 8 F 17 ) 2 ] 3 (Hong and Cai, 2009), NaHSO 4 (Jaberi and Hashemi, 2008), Al(HSO 4 ) 3 (Shaterian et al., 2007), P 2 O 5 or InCl 3 (Kumar et al., 2010), tetra-n-butylammonium bromide (TBAB) (Kantevari et al., 2008), nano-TiO 2 and BF 3 –SiO 2 (Mirjalili et al., 2008, 2011). Consequently, the synthesis of benzoxanthene derivatives, with the aim of developing new drug molecules has been an active area of research. "
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    ABSTRACT: Recoverable heterogeneous AgI nanoparticles efficiently catalyzed the one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes via multi-component reaction of aldehydes and 2-naphthol under solvent-free conditions. The present approach offers several advantages such as short reaction times, high yields, easy purification, reusability of the catalyst and low catalyst loading.
    Full-text · Article · Jun 2012 · Journal of Saudi Chemical Society
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    ABSTRACT: A solvent-free and efficient synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes through the one-pot condensation of β-naphthol and aldehydes catalyzed by recyclable and reusable Iron(III) triflate was reported. Notably, the presented method features short reaction time, excellent yield, and simple experimental procedure.
    No preview · Article · Sep 2012 · Research on Chemical Intermediates
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