Efficient One-Pot Synthesis of Some New Xanthene Derivatives Based on the Reaction of Dimedone with α,α′-Bis(substituted-benzylidene) Cycloalkanones Using Catalytic Amount of _pTSA

REFERENCES

• Hideo , T. Benzopyrano[2,3-b]xanthene derivatives. JP567 005480 . Jpn. Tokkyo Koho 1981 , 14 ; Chem. Abstr. 1981 , 95 , 80922b .
   Google Scholar
• Poupelin , J. P. ; Saint-Rut , G. ; Fussard-Blanpin , O. ; Narcisse , G. ; Uchida-Ernouf , G. ; Lakroix , R. Synthesis and antiinflammatory properties of bis(2-hydroxy-1-naphthyl)methane derivatives, I: Monosubstituted derivatives . Eur. J. Med. Chem. 1978 , 13 , 67 – 71 .
   Web of Science ®Google Scholar
• Jamison , J. M. ; Krabill , K. ; Hatwalkar , A. ; Jamison , E. ; Tsai , C. C. Potentiation of the antiviral activity of poly r(A-U) by xanthene dyes . Cell. Biol. Int. Rep. 1990 , 14 , 1075 – 1084 .
   PubMedGoogle Scholar
• (a) Griffiths , J. ; Lee , W. J. Synthesis, light absorption, and fluorescence properties of new thiazole analogues of the xanthene dyes . Dyes Pigments 2003 , 57 , 107 – 114 ; (b) Banerjee , A. ; Mukherjee , A. K. Chemical aspects of santalin as a histological stain . Stain. Technol. 1981 , 56 , 83 – 85 ; (c) Menchen , S. M. ; Benson , S. C. ; Lam , J. Y. L. ; Zhen , W. ; Sun , D. ; Rosenblum , B. B. ; Khan , S. H. ; Taing , M. Sulfonated diarylrhodamine dyes. U.S. Patent 6,583,168, 2003.
   Web of Science ®Google Scholar
• Knight , C. G. ; Stephens , T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles . Biochem. J. 1989 , 258 , 683 – 689 .
   PubMed Web of Science ®Google Scholar
• Ahmad , M. ; King , T. A. ; Ko , D.-K. ; Cha , B. H. ; Lee , J. Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases . J. Phys. D: Appl. Phys. 2002 , 35 , 1473 – 1476 .
   Web of Science ®Google Scholar
• (a) Zhou , J.-F. One-step synthesis of pyridine and 4H-pyran derivatives from bisarylidenecyclohexanone and malononitrile under microwave irradiation . Synth. Commun. 2003 , 33 , 99 – 103 ; (b) Wang , X. S. ; Shi , D. Q. ; Du , Y. ; Zhou , Y. ; Tu , S. J. Synthesis of 2-aminopyran derivatives and 3-arylpropionitrile derivatives catalyzed by KF/Al2O3 . Synth. Commun. 2004 , 34 , 1425 – 1432 ; (c) Jin , T. S. ; Liu , L. B. ; Zhao , Y. ; Li , T. S. Clean, one-pot synthesis of 4H-pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media . Synth. Commun. 2005 , 35 , 1859 – 1863 .
   Web of Science ®Google Scholar
• (a) Raj , A. A. ; Raghuanathan , R. A novel entry into a new class of spiroheterocyclic framework: Regioselective synthesis of dispiro[oxindole-cyclohexanone]pyrrolidines and dispiro[oxindole-hexahydroindazole]pyrrolidines. Tetrahedron 2001, 57, 10293–10298; (b) Girgis , A. S. Regioselective synthesis and stereochemical structure of anti-tumor active dispiro[3H-indole-3,2′-pyrrolidine-3′,3″-piperidine]-2(1H),4″-diones. Eur. J. Med. Chem. 2009, 44, 1257–1264.
   Web of Science ®Google Scholar
• Ahmed , M. G. ; Ahmed , S. A. ; Uddin , M. K. ; Rahman , M. T. ; Fujio , M. ; Tsuda , Y. A facile synthesis of fused spiroketal skeleton: 2,2′-Spirobi(4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydrochroman) . Tetrahedron Lett. 2005 , 46 , 8217 – 8220 .
   Web of Science ®Google Scholar
• (a) Longhi , K. ; Moreira , N. ; Morzari , M. R. B. ; Floss , V. M. ; Bonacorso , H. G. ; Zanatta , N. ; Martins , M. A. P. An efficient solvent-free synthesis of NH-pyrazoles from β-dimethylaminovinylketones and hydrazine on grinding . Tetrahedron Lett. 2010 , 51 , 3193 – 3196 ; (b) Huang , P.-J. J. ; Cameron , T. S. ; Jha , A. Novel synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyran . Tetrahedron Lett. 2009 , 50 , 51 – 54 ; (c) Mogilaiah , K. ; Chowdary , D. S. ; Redday , P. R. ; Redday , N. V. Mild and efficient synthesis of phthalazine-1,4-diones using pTSA in the solid state . Synth. Commun. 2003 , 33 , 127 – 131 .
   Web of Science ®Google Scholar
• Karimi-Jaberi , Z. ; Pooladian , B. A facile synthesis of α,α ′-bis(substituted benzylidene) cycloalkanones catalyzed by p-TSA under solvent-free conditions . Green Chem. Lett. Rev. 2012 , 5 , 187 – 193 .
   Web of Science ®Google Scholar