Facile and Efficient Method for the Synthesis of 14-Substituted-14-H-dibenzo[a,j]xanthenes Catalyzed by Ruthenium Chloride Hydrate as a Homogeneous Catalyst

REFERENCES

• Dimmock , J. R. ; Raghavan , S. K. ; Bigam , G. E. Evaluation of Mannich bases of 2-arylidene-1,3-diketones versus murine P388 leukemia . Eur. J. Med. Chem. 1988 , 23 , 111 – 117 .
   Web of Science ®Google Scholar
• Koeller , K. M. ; Haggarty , S. J. ; Perkins , B. D. ; Leykin , I. ; Wong , J. C. ; Kao , M. C. J. ; Schreiber , S. L. Chemical genetic modifier screens: Small molecule trichostatin suppressors as probes of intracellular histone and tubulin acetylation . Chem. Biol. 2003 , 10 , 397 – 410 .
   PubMed Web of Science ®Google Scholar
• Katritzky , A. R. ; Czerney , P. ; Levell , J. R. Benzotriazole-mediated conversions of para-H-substituted pyrylium, benzo[b]pyrylium, and xanthylium salts into para-position functionalized derivatives (an indirect electrophilic substitution of electron-deficient heteroaromatics). J. Org. Chem. 1997, 62, 8198–8200.
   PubMed Web of Science ®Google Scholar
• Alcantara-Licudine , J. P. ; Kawate , M. K. ; Li , Q. X. Method for the analysis of phloxine B, uranine, and related xanthene dyes in soil using supercritical fluid extraction and high-performance liquid chromatography . J. Agric. Food Chem. 1997 , 45 , 766 – 773 .
   Web of Science ®Google Scholar
• Sen , R. N. ; Sarkar , N. N. The condensation of primary alcohols with resorcinol and other hydroxy aromatic compounds . J. Am. Chem. Soc. 1925 , 47 , 1079 – 1091 .
   Web of Science ®Google Scholar
• Van Allan , J. A. ; Giannini , D. D. ; Whitesides , T. H. Dibenzoxanthene derivatives and related products from β-naphthol and aldehydes or acetals . J. Org. Chem. 1982 , 47 , 820 – 823 .
   Web of Science ®Google Scholar
• Ota , K. ; Kito , T. An improved synthesis of dibenzoxanthene . Bull. Chem. Soc. Jpn. 1976 , 49 , 1167 – 1168 .
   Web of Science ®Google Scholar
• Khosropour , A. R. ; Khodaei , M. M. ; Moghannian , H. A facile, simple, and convenient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent free conditions . Synlett 2005 , 955 – 958 .
   Web of Science ®Google Scholar
• Rajitha , B. ; Kumar , B. S. ; Reddy , Y. T. ; Reddy , P. N. ; Sreenivasulu , N. Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation . Tetrahedron Lett. 2005 , 46 , 8691 – 8693 .
   Web of Science ®Google Scholar
• Sarma , R. J. ; Baruah , J. B. One-step synthesis of dibenzoxanthenes . Dyes Pigments 2005 , 64 , 91 – 92 .
   Web of Science ®Google Scholar
• Ko , S. ; Yao , C.-F. Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibebzo[a,j]xanthenes under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 8827 – 8829 .
   Web of Science ®Google Scholar
• Saini , A. ; Kumar , S. ; Sandhu , J. S. A new LiBr-catalyzed facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating . Synlett 2006 , 1928 – 1932 .
   Web of Science ®Google Scholar
• Das , B. ; Ravikanth , B. ; Ramu , R. ; Laxminarayana , K. ; Rao , B. V. Iodine-catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes . J. Mol. Catal. A: Chem. 2006 , 255 , 74 – 77 .
   Web of Science ®Google Scholar
• Bigdeli , M. A. ; Heravi , M. M. ; Mahdavinia , G. H. Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes . Catal. Commun. 2007 , 8 , 1595 – 1598 .
   Web of Science ®Google Scholar
• Nagarapu , L. ; Kantevari , S. ; Mahankhali , V. C. ; Apuri , S. Potassium dodecatungstocobaltate trihydrate (K5COW12O40 · 3H2O): A mild and efficient reusable catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation . Catal. Commun. 2007 , 8 , 1173 – 1177 .
   Web of Science ®Google Scholar
• Bigdeli , M. A. ; Heravi , M. M. ; Mahdavinia , G. H. Silica-supported perchloric acid (HClO4-SiO2): A mild, reusable, and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes . J. Mol. Catal. A: Chem. 2007 , 275 , 25 – 29 .
   Web of Science ®Google Scholar
• Shaterian , H. R. ; Ghashang , M. ; Hassankhani , A. One-pot synthesis of aryl 14H-dibenzo[a,j]xanthene leuco-dye derivatives . Dyes Pigments 2008 , 76 , 564 – 568 .
   Web of Science ®Google Scholar
• Su , W. ; Yang , D. ; Jin , C. ; Zhang , B. Yb(OTf)3-catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: A green synthesis of aryl-14H-dibenzo[a,j]xanthenes . Tetrahedron Lett. 2008 , 49 , 3391 – 3394 .
   Web of Science ®Google Scholar
• Dabiri , M. ; Baghbanzadeh , M. ; Shakouri Nikcheh , M. ; Arzroomchilar , E. Ecofriendly and efficient one-pot synthesis of alkyl-or aryl-14H-dibenzo[a,j]xanthenes in water . Bioorg. Med. Chem. Lett. 2008 , 18 , 436 – 438 .
   PubMed Web of Science ®Google Scholar
• Kantevari , S. ; Mahankhali , V. C. ; Rudra Das , A. P. ; Vuppalapati , S. V. N. ; Lingaiah , N. Catalysis by an ionic liquid: Highly efficient solvent-free synthesis of aryl-14H-dibenzo[a,j]xanthenes by molten tetrabutylammonium bromide under conventional and microwave heating . Catal. Commun. 2008 , 9 , 1575 – 1578 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Bakhtiari , K. ; Daroogheha , Z. ; Bamoharram , F. F. Facile heteropolyacid-promoted synthesis of 14-substituted-14H-dibenzo[a,j]xanthene derivatives under solvent-free conditions. J. Mol. Catal. A: Chem. 2007, 273, 99–101.
   Web of Science ®Google Scholar
• Imani Shakibaei , G. ; Mirzaei , P. ; Bazgir , A. Dowex-50 W promoted synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions . Appl. Catal. A: Gen. 2007 , 325 , 188 – 192 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Khorshidi , A. Efficient RuIII-catalyzed condensation of indoles and aldehydes or ketones . Can. J. Chem. 2006 , 84 , 1541 – 1545 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Khorshidi , A. Ultrasonic-assisted ruthenium-catalyzed oxidation of aromatic and heteroaromatic compounds . Catal. Commun. 2008 , 9 , 416 – 420 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Khorshidi , A. RuIII-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones . J. Mol. Catal. A: Chem. 2007 , 270 , 112 – 116 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Khorshidi , A. Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles . Tetrahedron Lett. 2008 , 49 , 1450 – 1454 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Khorshidi , A. Ruthenium-catalyzed efficient routes to oxindole derivatives . Can. J. Chem. 2009 , 87 ( 9 ), 1213 – 1217 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Keshavarz , E. Ruthenium-catalyzed cross-aldol reaction with aldehydes and ketones . Arkivoc 2009 , 2 , 68 – 75 .
   Google Scholar
• Murahashi , S.-I. Ruthenium in Organic Synthesis; Wiley-VCH : New York , 2004 .
   Google Scholar
• Bruneau , C. ; Dixneuf , P. H. Ruthenium Catalysts and Fine Chemistry ; Springer : Berlin , 2004 .
   Google Scholar
• Murai , S. Activation of Unreactive Bonds and Organic Synthesis ; Springer : Berlin , 1999 .
   Google Scholar