Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 3
680
Views
21
CrossRef citations to date
0
Altmetric
Original Articles

Ionic Liquid as Catalyst and Reaction Medium: A Simple and Efficient Procedure for Paal–Knorr Furan Synthesis

, , &
Pages 370-377 | Received 21 Jan 2009, Published online: 06 Jan 2010

REFERENCES

  • Donnelly , D. M. ; Meegan , M. J. Comprehensive Heterocyclic Chemistry ; Pergamon : Oxford , 1984 ; vol. 4 , pp. 705 – 709 .
  • Michael , H. S. ; Michael , R. ; Stefan , F. K. Gold(I)-catalyzed synthesis of highly substituted furans . Org. Lett. 2005 , 7 , 3925 – 3927 , and references therein .
  • Lipshutz , B. H. Five-membered heteroaromatic rings as intermediates in organic synthesis . Chem. Rev. 1986 , 86 , 795 – 819 .
  • Rao , H. S. P. ; Jothilingam , S. Facile microwave-mediated transformations of 2-butene-1,4-diones and 2-butyne-1,4-diones to furan derivatives . J. Org. Chem. 2003 , 68 , 5392 – 5394 .
  • Hou , X. L. ; Cheung , H. Y. ; Hon , T. U. ; Kwan , P. L. ; Lo , T. H. ; Tong , S. Y. ; Wong , H. N. C. Regioselective syntheses of substituted furans . Tetrahedron 1998 , 54 , 1955 – 2020 .
  • Gilchrist , T. L. Synthesis of aromatic heterocycles . J. Chem. Soc., Perkin Trans. 1 1999 , 2849 – 2866 .
  • Ceylan , M. ; Gurdere , M. B. ; Budak , Y. ; Kazaz , C. ; Seçen , H. One-step preparation of symmetrical 1,4-diketones from α-halo ketones in the presence of Zn-I2 as a condensation agent . Synthesis 2004 , 1750 – 1754 .
  • Mackay , D. ; Neeland , E. G. ; Taylor , N. J. Michael adducts of a half-blocked enedione as sources of 3-substituted 2,5-diketones and 2,5-dialkylfurans . J. Org. Chem. 1986 , 51 , 2351 – 2361 .
  • Minetto , G. ; Raveglia , L. F. ; Taddei , M. Microwave-assisted Paal–Knorr reaction: A rapid approach to substituted pyrroles and furans . Org. Lett. 2004 , 6 , 389 – 392 .
  • Sato , T. ; Okazaki , H. ; Otera , J. ; Nozaki , H. A new strategy for 1,4- and 1,4,7-polycarbonyl compounds . J. Am. Chem. Soc. 1988 , 110 , 5209 – 5211 .
  • Ballini , R. ; Bartoli , G. A new, simple, and general synthesis of 1,3-, 1,4-, and 1,5-diketones from functionalized nitroalkanes . Synthesis 1993 , 965 – 967 .
  • Stetter , H. ; Jonas , F. Addition von aldehyden an aktivierte doppelbindungen XXV: Synthesen und reaktionen von verzweigten tricarbonyl-verbindungen . Chem. Ber. 1981 , 114 , 564 – 580 .
  • Chiu , P. K. ; Sammes , M. P. Lancifodilactone A, a novel bisnortriterpenoid from Schisandra lancifolia . Tetrahedron 1988 , 44 , 3531 – 3538 .
  • Yasuda , M. ; Katoh , Y. ; Shibata , I. ; Baba , A. ; Matsuda , H. ; Sonoda , N. NMR studies of five-coordinate tin enolate: An efficient reagent for halo selective reaction toward. α-halo ketone or. α-halo imine . J. Org. Chem. 1994 , 59 , 4386 – 4392 .
  • Yasuda , M. ; Tsuji , S. ; Shibata , I. ; Baba , A. Synthesis of 1,4-diketones: Unusual coupling of tin enolates with α-chloro ketones catalyzed by zinc halides . J. Org. Chem. 1997 , 62 , 8282 – 8283 .
  • Kelin , A. V. ; Kulinkovich , O. G. A new simple synthesis of aryl-substituted 1,4-diketones . Synthesis 1996 , 330 – 332 .
  • Natali , N. M. ; Kelin , A. V. ; Kulinkovich , O. G. One-step preparation of 1,4-diketones from methyl ketones and α-bromomethyl ketones in the presence of ZnCl2·t-BuOH·Et2NR as a condensation agent. Synthesis 2000, 1259–1262.
  • Hegedus , L. S. ; Perry , R. J. Phosphinecarbonylnitrosylacylcobaltate complexes as acyl transfer reagents: Acylation of allylic halides, conjugated enones, and quinones . J. Org. Chem. 1985 , 50 , 4955 – 4960 .
  • Drewes , S. E. ; Hogan , C. J. Furan derivatives from cyclodehydration of brackein-like 1,4-dicarbonyl compounds . Synth. Commun. 1989 , 19 , 2101 – 2107 .
  • Raghavan , S. ; Anuradha , K. Solid-phase synthesis of heterocycles from 1,4-diketone synthons . Synlett 2003 , 711 – 713 .
  • Banik , B. K. ; Samajdar , S. ; Banik , I. Simple synthesis of substituted pyrroles . J. Org. Chem. 2004 , 69 , 213 – 216 .
  • Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 – 2084 .
  • Wasserscheid , P. ; Keim , W. Ionic liquids–New solutions for transition metal catalysis . Angew. Chem. Int. Ed. 2000 , 39 , 3772 – 3789 .
  • Jain , N. ; Kumar , A. ; Chauhan , S. ; Chauhan , S. M. S. Chemical and biochemical transformations in ionic liquids . Tetrahedron 2005 , 61 , 1015 – 1060 .
  • Gu , Y. ; Shi , F. ; Deng , Y. Ionic liquid as an efficient promoting medium for fixation of CO2: Clean synthesis of α-methylene cyclic carbonates from CO2 and propargyl alcohols catalyzed by metal salts under mild conditions . J. Org. Chem. 2004 , 69 , 391 – 394 .
  • Kim , Y. J. ; Varma , R. S. Tetrahaloindate(III)-based ionic liquids in the coupling reaction of carbon dioxide and epoxides to generate cyclic carbonates: H-bonding and mechanistic studies . J. Org. Chem. 2005 , 70 , 7882 – 7891 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Eeshwaraiah , B. ; Gupta , M. K. Bi(OTf)3/[bmim]BF4 as novel and reusable catalytic system for the synthesis of furan, pyrrole, and thiophene derivatives . Tetrahedron Lett. 2004 , 45 , 5873 – 5876 .
  • Anzalone , P. W. ; Mohan , R. S. Trimethylsilyl trifluoromethanesulfonate catalyzed one-pot method for the conversion of aldehydes to homoallyl ethers in an ionic liquid . Synthesis 2005 , 2661 – 2663 .
  • Ranu , B. C. ; Jana , R. Catalysis by ionic liquid: A green protocol for the stereoselective debromination of vicinal-dibromides by [pmIm]BF4 under microwave irradiation . J. Org. Chem. 2005 , 70 , 8621 – 8624 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.