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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Microwave-Assisted K-10 Montmorillonite Clay–Mediated Knoevenagel Hetero-Diels–Alder Reactions: A Novel Protocol for the Synthesis of Polycyclic Pyrano[2,3,4-kl]xanthene Derivatives

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Pages 613-625 | Received 15 May 2008, Published online: 28 Jan 2009

REFERENCES

  • For reviews on the intramolecular Diels–Alder reaction, see (a) Roush , W. R. In Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon : Oxford , UK , 1991 ; vol. 5 , chapter 4.4 , pp. 513 – 550 ; (b) Fallis, A. Harvesting Diels and Alder's garden: Synthetic investigations of intramolecular [4 + 2] cycloadditions. Acc. Chem. Res. 1999, 32, 464.
  • (a) House , H. O. ; Cronin , T. H. A study of the intramolecular Diels–Alder reaction . J. Org. Chem. 1965 , 30 , 1061 ; (b) Roush , W. R. Total synthesis of (±)-dendrobine . J. Am. Chem. Soc. 1978 , 100 , 3599 ; (c) Roush , W. R. ; Peseckis , S. M. Intramolecular Diels–Alder reactions: The angularly methylated trans-perhydroindan ring system . J. Am. Chem. Soc. 1981 , 103 , 6696 ; (d) Shea , K. J. ; Gilman , J. W. Lewis acid–catalysed intramolecular Diels-Alder cycloadditions: A mild method for the synthesis of bicyclo [n.3.1] bridgehead alkenes . Tetrahedron Lett. 1983 , 24 , 657 .
  • Ion , R. M. ; Fara , V. L. Photophysical and photochemical properties of dye molecules in polymers used for fluorescent solar concentrators. Proc. Indian Acad. Sci. 1995, 107, 825.
  • Sirkecioglu , O. ; Tulinli , N. ; Akar , A. Synthesis of 14-alkyl-14H-dibenzo[a,j]xanthenes . J. Chem. Res., Synop. 1995 , 502 .
  • Ion , R. M. PDT—A photosensitization or a photocatalytic process . Prog. Catal. 1997 , 2 , 55 .
  • Ion , R. M. ; Frackowiak , D. ; Plannar , A. ; Wiktorowicz , K. The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption, and emission spectroscopy . Acta Biochim. Pol. 1998 , 45 , 833 .
  • Hideu , T. [1]Benzopyrano[2,3-b]xanthene derivatives . Jpn. Tokkyo Koho JP 56005480, 27 June 1979 ; Chem. Abstr. 1981 , 95 , 80922b .
  • Lamberk , R. W. ; Martin , J. A. ; Merrett , J. H. ; Parkes , K. E. B. ; Thomas , G. J. Preparation of pyrimidine nucleosides as thymidine kinase inhibitors and virucides . PCT Int. Appl. WO 9706178, 1997 ; Chem. Abstr. 1997 , 126 , P212377y .
  • Poupelin , J. P. ; Saint-Rut , G. ; Fussard-Blanpin , O. ; Narcisse , G. ; Uchida- Ernouf , G. ; Lakroix , R. Action of hemolysin from Pseudomonas aeruginosa on the Ehrich ascites tumor cells . Eur. J. Med. Chem. 1978 , 13 , 67 – 71 .
  • Rathna Durga , R. ; Jayashankaran , J. ; Raghunathan , R. A rapid access to indolo[2,1-a]pyrrolo[4′,3′:4,5]pyrano[5,6-c]coumarin/[6,5-c]chromone derivatives by domino Knoevenagal intramolecular hetero-Diels–Alder reactions . Tetrahedron Lett. 2007 , 48 , 1385 – 1389 .
  • Jayashankaran , J. ; Rathna Durga , R. ; Raghunathan , R. An efficient synthesis of thiopyrano[5,6-c]coumarin/[6,5-c]chromones through intramolecular domino Knoevenagel hetero-Diels–Alder reactions . Tetrahedron Lett. 2006 , 47 , 2265 – 2270 .
  • Sugi Kamala , E. T. ; Nirmala , S. ; Sudha , L. ; Ramesh , E. ; Raghunathan , R. Actacis-3-methyl-1-phenyl-8a,9,10,11,12,12a,12b-hexahydro-1H,3bH-pyrazolo[3,4:2′,3′]pyrano[4′,5′,6′-kl]xanthene . Cryst. E Acta Cryst. 2008 , E64 , o245 – o246 .
  • Ramesh , E. ; Kathiresan , M. ; Raghunathan , R. Solvent-free microwave-assisted conversion of Baylis–Hillman adducts of ninhydrin into functionalized spiropyrrolidines/pyrrolizidines through 1,3-dipolar cycloaddition . Tetrahedron Lett. 2007 , 48 , 1835 – 1839 .
  • Jayashankaran , J. ; Rathna DurgaR. S. , Manian ; Raghunathan , R. A facile synthesis of novel dispiroheterocycles through solvent-free microwave-assisted [3 + 2] cycloaddition of azomethine ylides . Tetrahedron Lett. 2004 , 45 , 7303 – 7305 .
  • Jayashankaran , J. ; Rathna DurgaR. S. , Manian ; Raghunathan , R. A regioselective synthesis of dispiro[oxindole-cyclohexanone]pyrrolidines and dispiro[oxindole-hexahydroindazole]pyrrolidines by sequential 1,3-dipolar cycloaddition and annulation through a microwave induced solvent-free approach . Tetrahedron 2005 , 61 , 5595 – 5598 .
  • Tietze , L. F. ; Stegelmeier , H. ; Harms , K. ; Brumby , T. Control of the conformation of transition states in intramolecular Diels-Alder reactions with inverse electron demand . Angew. Chem. Int. Ed. 1982 , 21 , 863 .

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