Abstract
A simple and efficient one-pot process for the synthesis of 1,8-dioxo-octahydroxanthene and 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives via the Knoevenagel–Michael cascade reactions of aromatic aldehydes and dimedone catalyzed by Bronsted acidic ionic liquids (BAILs) in solvent-free and aqueous conditions is described in this study. These heterocycles were prepared in the presence of Bronsted acidic ionic liquids as a suitable, economical, readily synthesized and eco-friendly catalyst. This method offers several advantages such as high yields, simplicity of the workup, low cost, short reaction times, green conditions and use of a reusable catalyst.
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Agnes B, Peter H, Eberhardt H, Stephan DH, Wolfgang AH (2008) Acceptor substituted N-heterocyclic carbenes and their Rh(I)complexes: synthesis, structure and properties. J Organomet Chem 693:2079–2090
Ashtarian J, Heydari R, Maghsoodlou MT, Yazdani Elah Abadi A (2019) An efficient synthesis of 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives using baker′s yeast. Rev Roum Chim 64:259–264
Bigdeli M (2010) Clean synthesis of 1,8-dioxooctahydroxanthenes promoted by DABCO-bromine in aqueous media. Chin Chem Lett 21:1180–1182
Chowdhury S, Mohan RS, Scott JL (2007) Reactivity of ionic liquids. Tetrahedron 63:2363–2389
Dabiri M, Baghbanzadeh M, Arzroomchilar E (2008) 1-Methylimidazolium trifluoroacetate ([Hmim]TFA): an efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines. Catal Commun 9:939–942
Das B, Thirupathi P, Mahender I, Reddy VS, Rao YK (2006) Amberlyst-15: an efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxooctahydroxanthenes and 1,8-dioxo-decahydroacridines. J Mol Catal A Chem 247:233–239
Das B, Kashanna J, Kumar RA, Jangili P (2012) Efficient organocatalytic synthesis of 1,8-dioxo-octahydroxanthenes. Synth Commun 42:2876–2884
Eichmann M, Keim W, Haumann M, Melcher BU, Wasserscheid P (2009) Nickel catalyzed dimerization of propene in chloroaluminate ionic liquids: Detailed kinetic studies in a batch reactor. J Mol Catal A Chem 314:42–48
Esmaeilpour M, Javidi J, Dehghani F, Nowroozi Dodeji F (2014) Fe3O4@SiO2–imid–PMAn magnetic porous nanospheres as recyclable catalysts for the one-pot synthesis of 14-aryl- or alkyl-14H-dibenzo[a, j]xanthenes and 1,8-dioxooctahydroxanthene derivatives under various conditions. New J Chem 38:5453–5461
Fan XS, Hu XY, Zhang XY, Wang JJ (2005a) InCl3·4H2O-promoted green preparation of xanthenedione derivatives in ionic liquids. Can J Chem 83:16–20
Fan XS, Li YZ, Zhang XY, Hu XY, Wang JJ (2005b) FeCl3·6H2O catalyzed condensation of aromatic aldehydes with 5,5-dimethyl-1,3-cyclohexanedione in ionic liquids. ChinJ Org Chem 25:1482–1486
Fang D, Gong K, Liu Z (2009) Synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by acidic ionic liquids in aqueous media. Catal Lett 127:291–295
Girijesh KV, Keshav R, Rajiv KV, Pratibha D, Singh MS (2011) An efficient one-pot solvent-free synthesis and photophysical properties of 9-aryl/alkyl-octahydroxanthene-1,8-diones. Tetrahedron 67:3698–3704
Gong K, Wang H, Wang S, Wang Y, Chen J (2015) Efficient synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by β-cyclodextrin grafted with butyl sulfonic acid in aqueous media. Chin J Catal 36:1249–1255
Hajipour AR, Leila K, Arnold ER (2008) Bronsted acidic ionic liquid as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions. Catal Commun 9:89–96
Hamada Y, Matsuura F, Oku M, Hatano K, Shioiri T (1997) Synthesis and application of new chiral bidentate phosphine, 2,7-di-tert-butyl-9,9-dimethyl-4,5-bis(methylphenylphosphino) xanthene. Tetrahedron Lett 38:8961–8964
Hapiot P, Lagrost C (2008) Electrochemical reactivity in room-temperature ionic liquids. Chem Rev 108:2238–2264
Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J (2010) Catalyst-free one-pot four component synthesis of polysubstitutedimidazoles in neutral ionic liquid 1-butyl-3-methylimidazolium bromide. J Comb Chem 12:844–849
Ilangovan A, Muralidharan S, Sakthivel P, Malayappasamy S, Karuppusamy S, Kaushik MP (2013) Simple and cost effective acid catalysts for efficient synthesis of 9-aryl-1,8-dioxooctahydroxanthene. Tetrahedron Lett 54:491–494
Ion RM, Planner A, Wiktorowicz K, Frackowiak D (1998) The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy. Acta Biochem Pol 45:833–845
Iranpoor N, Firouzabadi H, Azadi R (2007) An Imidazolium-based phosphinite Ionic Liquid (IL-OPPh2) as a reusable reaction medium and Pd (II) ligand in heck reactions of aryl halides with styrene and n-butyl acrylate. Eur J Org Chem 13:2197–2201
Jamison JM, Krabill K, Hatwalkar A, Jamison E, Tsai C (1990) Potentiation of theantiviral activity of poly r(A-U) by xanthene dyes. Cell Biol Int Rep 14:1075–1084
Javid A, Heravi MM, Bamoharram FF (2011a) One-pot synthesis of 1,8-dioxo-octahydroxanthenes utilizing silica-supported Preyssler nano particles as novel and efficient reusable heterogeneous acidic catalyst. Eur J Chem 8:910–916
Javid A, Heravi MM, Bamoharram FF (2011b) One-pot synthesis of tetra substituted imidazoles catalyzed by preyssler type heteropoly acid. Eur J Chem 8:547–552
Jin TS, Zhang JS, Xiao JC, Wang AQ, Li TS (2004) Clean synthesis of 1,8-dioxooctahydroxanthene derivatives catalyzed by p-dodecylbenzenesulfonic acid in aqueous media. Synlett 5:866–870
Jin TS, Zhang JS, Wang AQ, Li TS (2005) Solid-state condensation reactions between aldehydes and 5,5-dimethyl-1,3-cyclohexanedione by grinding at room temperature. Synth Commun 35:2339–2345
John A, Yadav PJP, Palaniappan S (2006) Clean synthesis of 1,8-dioxo-dodecahydroxanthene derivatives catalyzed by polyaniline-p-toluenesulfonate salt in aqueous media. J Mol Catal A Chem 248:121–125
Kaiser C, Pavloff AM, Garvey E, Fowler PJ, Tedeschi DH, Zirkle CL (1972) Effect of structure upon neuropharmacological activity of some chlorpromazine analogs of the diphenylmethane type. J Med Chem 15:665–673
Kalantari M (2012) Synthesis of 1,8-dioxo-octahydroxanthenes and bis(indolyl)-methanes catalyzed by [Et3NH][H2PO4] as a cheap and mild acidic ionic liquid. Arabian J Chem 5:319–323
Kantevari S, Bantu R, Nagarapu L (2006) TMSCl mediated highly efficient one-pot synthesis of octahydroquinazolinone and 1,8-dioxo-octahydroxanthene derivatives. ARKIVOC xvi:136–148
Kantevari S, Bantu R, Nagarapu L (2007) HClO4–SiO2 and PPA–SiO2 catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent-free conditions: scope and limitations. J Mol Catal A Chem 269:53–57
Karade HN, Sathe M, Kaushik MP (2007) An efficient synthesis of 1,8-dioxo-octahydroxanthenes using tetrabutylammonium hydrogen sulphate. ARKIVOC xiii:252–258
Karthikeyan G, Pandurangan A (2009) Heteropolyacid (H3PW12O40) supported MCM-41: an efficient solid acid catalyst for the green synthesis of xanthene dione derivatives. J Mol Catal A Chem 311:36–45
Khazaei A, Zolfigol MA, Moosavi-Zare AR, Zare A (2010) An efficient method for the nitration of phenols with NaNO2 in the presence of 3-methyl-1-sulfonic acid imidazolium chloride. Sci Prod Iran 17:31–36
Khazaei A, Moosavi-Zare AR, Mohammadi Z, Zare A, Khakyzadeh V, Darvishi G (2013) Efficient preparation of 9-aryl-1,8-dioxo-octahydroxanthenes catalyzed by nano-TiO2 with high recyclability. RSC Adv 3:1323–1326
Kim YJ, Varma RS (2005) Microwave assisted preparation of imidazolium-based tetrachloroindate (III) and their application in the tetrahydropyranylation of alcohols. Tetrahedron Lett 46:1467–1469
Kore R, Srivastava R (2011a) Synthesis and applications of highly efficient, reusable, sulfonic acid group functionalized Brönsted acidic ionic liquid catalysts. J Mol Catal A Chem 345:117–126
Kore R, Srivastava R (2011b) Synthesis and applications of novel imidazole and benzimidazole based sulfonic acid group functionalized Brönsted acidic ionic liquid catalysts. J Mol Catal A Chem 345:117–126
Li JT, Li YW, Song YL, Chen GF (2012) Improved synthesis of 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives catalyzed by urea under ultrasound. Ultrason Sonochem 19:1–4
LiX EliW (2008) A green approach for the synthesis of long chain aliphatic acid esters at room temperature. J Mol Catal A Chem 279:159–164
Ma JJ, Li JC, Tang RX, Zhou X, Wu QH, Wang C, Zhang MM, Li Q (2007a) Condensation of aromatic aldehydes with 1,3-cyclohexanedione catalyzed by NaHSO4 in ionic liquids. J Org Chem 27:640–642
Ma JJ, Zhou X, Zhang XH, Wang C, Wang Z, Li JC, Li Q (2007b) A green and efficient synthesis of 9-aryl-3,4,5,6,7,9-hexahydroxanthene-1,8-dione using a task-specific ionic liquid as dual catalyst and solvent. Aus J Chem 60:146–148
Ma J, Wang C, Wu Q, Tang R, Liu H, Li Q (2008) An efficient green synthesis of xanthenedione derivatives promoted by acidic ionic liquid. Heteroatom Chem 19:609–611
Mahdavinia GH, Bigdeli MA, SaeidiHayeniaz Y (2009) Covalently anchored sulfonic acid on silica gel (SiO2-R-SO3H) as an efficient and reusable heterogeneous catalyst for the one-pot synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. Chin Chem Lett 20:539–541
Malaise G, Barloy L, Osborn JA (2001) Synthesis of xanthene-derived diimine and iminophosphine compounds as potential chiral bidentate ligands. Tetrahedron Lett 42:7417–7419
Menchen SM, Benson SC, Lam JYL, Zhen W, Sun D, Rosenblum BB, Khan SH, Taing M (2003) U.S. Patent, US6583168, Chem Abstr 139:54287f
Mohammadpoor-Baltork I, Moghadam M, Mirkhani V, Tangestaninejad S, Tavakoli HR (2011) Highly efficient and green synthesis of 14-aryl(alkyl)-14H-dibenzo[a, j]xanthene and 1,8-dioxooctahydroxanthene derivatives catalyzed by reusable zirconyltriflate [ZrO(OTf)2] under solvent-free conditions. Chin Chem Lett 22:9–12
Mulakayala N, Murthy PVNS, Rambabu D, Aeluri M, Adepu R, Krishna GR, Reddy CM, Prasad KRS, Chaitanya M, Kumar CS, Rao MVB, Pal M (2012) Catalysis by molecular iodine: a rapid synthesis of 1,8-dioxo-octahydroxanthenes and their evaluation as potential anticancer agents. Bioorg Med Chem Lett 22:2186–2191
Nandre KP, Patil VS, Bhosale SV (2011) CsF mediated rapid condensation of 1,3-cyclohexadione with aromatic aldehydes: comparative study of conventional heating vs. ambient temperature. Chin Chem Lett 22:777–780
Niknam K, Damya M (2009) 1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4: an efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes. J Chin Chem Soc 56:659–665
Öchsner E, Schneider MJ, Meyer C, Haumann M, Wasserscheid P (2011) Challenging the scope of continuous, gas-phase reactions with supported ionic liquid phase (SILP) catalysts-asymmetric hydrogenation of methyl acetoacetate. Appl Catal A399:35–41
Olivier-Bourbigou H, Magna L, Morvan D (2010) Ionic liquids and catalysis: recent progress from knowledge to applications. Appl Catal A 373:1–56
Oskooie HA, Tahershamsi L, Heravi MM, Baghernejad B (2010) Cellulose sulfonic acid: an efficient heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes. Eur J Chem 7:717–720
Pavlinac J, Zupan M, Laali KK, Stavber S (2009a) Halogenation of organic compounds in ionic liquids. Tetrahedron 65:5625–5662
Pavlinac J, Zupan M, Stavber S (2009b) Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media. Molecules 14:2394–2409
Poupelin JP, Saint-Ruf G, Foussard-Blanpin O, Narcisse G, Uchida-Ernouf G, Lacroix R (1978) Synthesis and antiinflammatory properties of bis (2-hydroxy-1-naphthyl)methane derivatives I. Eur J Med Chem 13:67–71
Qiao YF, Okazaki T, Ando T, Mizoue K, Kondo K, Eguchi T, Kakinuma K (1998) Isolation and characterization of a new pyrano[3′,4′ 6,7]naphtho[1,2-b]xanthene antibiotic FD-594. J Antibiot 51:282–287
Rewcastle GW, Atwell GJ, Zhuang L, Baguley BC, Denny WA (1991) Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids. J Med Chem 34:217–222
Rogers RD, Seddon KR (2002) Ionic liquids: industrial applications to green chemistry. American Chemical Society, Washington
Rostamizadeh S, Amani AM, Mahdavinia GH, Amiri G, Sepehrian H (2010) Ultrasound promoted rapid and green synthesis of 1,8-dioxo-octahydroxanthenes derivatives using nanosized MCM-41-SO3H as a nanoreactor, nanocatalyst in aqueous media. Ultrason Sonochem 17:306–309
Sarma RJ, Baruah JB (2005) One step synthesis of dibenzoxanthenes. Dyes Pigment 64:91–92
Seyyedhamzeh M, Mirzaei P, Bazgir A (2008) Solvent-free synthesis of aryl-14H-dibenzo[a, j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst. Dyes Pigment 76:836–839
Shakibaei GI, Mirzaei P, Bazgir A (2007) Dowex-50 W promoted synthesis of 14-aryl-14H-dibenzo[a, j]xanthene and 1,8-dioxooctahydroxanthene derivatives under solvent-free conditions. Appl Catal A 325:188–192
Shaterian HR, Arman M, Rigi F (2011a) Domino Knoevenagel condensation, Michael addition, and cyclization using ionic liquid, 2-hydroxyethylammonium formate, as a recoverable catalyst. J Mol Liq 158:145–150
Shaterian HR, Ranjbar M, Azizi K (2011b) Synthesis of benzoxanthene derivatives using Brønsted acidic ionic liquids (BAILs), 2-pyrrolidonium hydrogen sulfate and (4-sulfobutyl)tris(4-sulfophenyl) phosphonium hydrogen sulfate. J Mol Liq 162:95–99
Shirini F, Yahyazadeh A, Mohammadi K (2014) One-pot synthesis of various xanthene derivatives using ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable catalyst under solvent-free conditions. Chin Chem Lett 25:341–347
Sivaguru P, Lalitha A (2014) Ceric ammonium nitrate supported HY-zeolite: an efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes. Chin Chem Lett 25:321–323
Song GY, Wang B, Luo HT, Yang LM (2007) Fe3+-montmorillonite as a cost-effective and recyclable solid acidic catalyst for the synthesis of xanthenediones. Catal Commun 8:673–676
Tu SJ, Zhou JF, Lu ZS, Deng X, Shi DQ, Wang SH (2002) Condensation of aromatic aldehyde with 5,5 dimethyl 1,3 cyclohexandione without catalyst. Synth Commun 32:3063–3067
Wasserscheid P, Keim W (2000) Ionic liquids new solutions for transition metal catalysis. Angew Chem Int Ed 39:3772–3789
Wasserscheid P, Welton T (2008) Ionic liquids in synthesis. Wiley-VCH, Weinheim
Zare A, Hasaninejad A, Moosavi Zare AR, Parhami A, Sharghi H, Khalafi-Nezhad A (2007) Zinc oxide as a new, highly efficient, green, and reusable catalyst for microwave-assisted Michael addition of sulfonamides to α, β-unsaturated esters in ionic liquids. Can J Chem 85:438–444
Zare A, Moosavi-Zare AR, Hasaninejad A, Parhami A, Khalafi-Nezhad A, Beyzavi MH (2009a) Green, catalyst-free protocol for the efficient synthesis of N-sulfonyl aldimines and ketimines in ionic liquid [bmim] Br. Synth Commun 39:3156–3165
Zare A, Parhami A, Moosavi-Zare AR, Hasaninejad A, Khalafi-Nezhad A, Beyzavi MH (2009b) A catalyst-free protocol for the green and efficient condensation of indoles with aldehydes in ionic liquids. Can J Chem 87:416–421
Zhang ZH, Liu YH (2008) Antimony trichloride/SiO2 promoted synthesis of 9-ary-3,4,5,6,7,9-hexahydroxanthene-1,8-diones. Catal Commun 9:1715–1719
Zhang ZH, Tao XY (2008) 2,4,6-Trichloro-1,3,5-triazine-promoted synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions. Aus J Chem 61:77–79
Zhou ZQ, Deng XC (2013) [Et3NH][HSO4] catalyzed efficient and green synthesis of 1, 8-dioxo-octahydroxanthenes. J Mol Catal A Chem 367:99–102
Zolfigol MA, Khazaei A, Moosavi-Zare AR, Zare A (2010a) Ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride as a novel and highly efficient catalyst for the very rapid synthesis of bis(indolyl)methanes under solvent-free conditions. Org Prep Proc Int 42:95–102
Zolfigol MA, Khazaei A, Moosavi-Zare AR, Zare A (2010b) 3-Methyl-1-Sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature. J Iran Chem Soc 7:646–651
Zolfigol MA, Khazaei A, Moosavi-Zare AR, Zare A, Khakyzadeh V (2011) Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts. Appl Catal A 400:70–81
Zolfigol MA, Khakyzadeh V, Moosavi-Zare AR, Zare A, Azimi SB, Asgari Z, Hasaninejad A (2012) Preparation of various xanthene derivatives over sulfonic acid functionalized imidazolium salts (SAFIS) as novel, highly efficient and reusable catalysts. C R Chim 15:719–736
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We are thankful to the University of Sistan and Baluchestan Research Council for the partial support of this research.
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Ashtarian, J., Heydari, R., Maghsoodlou, MT. et al. Bronsted Acidic Ionic Liquids (BAILs)-Catalyzed Synthesis of 1,8-Dioxo-Octahydroxanthene and 2,2′-Arylmethylene Bis(3-Hydroxy-5,5-Dimethyl-2-Cyclohexene-1-One) Derivatives Under Eco-Friendly Conditions. Iran J Sci Technol Trans Sci 44, 51–64 (2020). https://doi.org/10.1007/s40995-019-00786-2
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DOI: https://doi.org/10.1007/s40995-019-00786-2