Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 21
359
Views
21
CrossRef citations to date
0
Altmetric
Original Articles

Efficient and Green Approaches for the Synthesis of 4H-Benzo[g]chromenes in Water, Under Neat Conditions, and Using Task-Specific Ionic Liquid

, &
Pages 3211-3219 | Received 22 Jan 2011, Published online: 17 Aug 2012

REFERENCES

  • Elinson , M. N. ; Dorofeev , A. S. ; Feducovich , S. K. ; Gorbunov , S. V. ; Nasybullin , R. F. ; Stepanov , N. O. Electrochemically induced chain transformation of salicylaldehydes and alkyl cyanoacetates into substituted 4H-chromenes . Tetrahedron Lett. 2006 , 47 , 7629 – 7633 .
  • Sun , W. ; Cama , L. J. ; Birzin , E. T. ; Warrier , S. ; Locco , L. ; Mosley , R. ; Hammond , M. L. ; Rohrer , S. P. 6H-Benzo[c]chromen-6-one derivatives as selective ERβ agonists . Bioorg. Med. Chem. Lett. 2006 , 16 , 1468 – 1472 .
  • Stachulski , A. V. ; Berry , N. G. ; Low , A. C. L. ; Moores , S. L. ; Row , E. ; Warhurst , D. C. ; Adagu , I. S. ; Rossignol , J.-F. Identification of isoflavone derivatives as effective anticryptosporidial agents in vitro and in vivo. J. Med. Chem. 2006, 49, 1450–1454.
  • Moon , D. O. ; Choi , Y. H. ; Kim , N. D. ; Park , Y. M. ; Kim , G. Y. Anti-inflammatory effects of β-lapachone in lipopolysaccharide-stimulated BV2 microglia . Int. Immunopharmacol. 2007 , 7 , 506 – 514 .
  • De Andrade-Neto , V. F. ; Goulart , M. O. F. ; Da Silva Filho , J. F. ; Da Silva , M. J. ; Pinto , M. D. C. F. R. ; Pinto , A. V. Antimalarial activity of phenazines from lapachol, β-lapachone, and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo . Bioorg. Med. Chem. Lett. 2004 , 14 , 1145 – 1149 .
  • Elisa , P. S. ; Ana , E. B. ; Ravelo , A. G. ; Yapu , D. J. ; Turba , A. G. Antiplasmodial activity of naphthoquinones related to lapachol and β-lapachone . Chem. Biodiv. 2005 , 2 , 264 .
  • Ough , M. ; Lewis , A. ; Bey , E. A. ; Gao , J. ; Ritchie , J. M. ; Bornmann , W. ; Oberley , L. W. ; Cullen , J. J. Efficacy of β-lapachone in pancreatic cancer treatment: Exploiting the novel, therapeutic target NQO1 . Canc. Biol. Ther. 2005 , 4 , 94 – 101 .
  • Li , C. J. ; Li , Y. L. U.S. Patent Appl. 2005222246A1 20051006, 2005.
  • Shestopalov , A. M. ; Emelianova , Y. M. ; Nesterov , V. N. One-step synthesis of substituted 2-amino-5,6,7,8-tetrahydro-4H-benzo[b]pyrans: Molecular and crystal structure of 2-amino-3-(2-methoxyethoxycarbonyl)-4-(2-nitro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran . Russ. Chem. Bull. 2003 , 52 , 1164 – 1172 .
  • Qabaja , G. ; Jones , G. B. Annulation strategies for benzo[b]fluorene synthesis: Efficient routes to the kinafluorenone and WS-5995 antibiotics . J. Org. Chem. 2002 , 65 , 7187 – 7194 .
  • Da Silva , A. J. M. ; Buarque , C. D. ; Brito , F. V. ; Aurelian , L. ; Macedo , L. F. ; Malkas , L. H. ; Hickey , R. J. ; Lopes , D. V. S. ; Noël , F. ; Murakami , Y. L. B. ; Silva , N. M. V. ; Melo , P. A. ; Caruso , R. R. B. ; Castro , N. G. ; Costa , P. R. R. Synthesis and preliminary pharmacological evaluation of new (±)-1,4-naphthoquinones structurally related to lapachol . Bioorg. Med. Chem. 2002 , 10 , 2731 – 2738 .
  • Rueping , M. ; Sugiono , E. ; Merino , E. Asymmetric iminium ion catalysis: An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones . Angew. Chem. Int. Ed. 2008 , 47 , 3046 – 3049 .
  • Armstrong , J. J. ; Turner , W. B. The structure of lambertellin . J. Chem. Soc. 1965 , 5927 – 5930 .
  • Brown , P. M. ; Krishnamoorthy , V. ; Mathieson , J. W. ; Thomson , R. H. Naturally occurring quinones, part XVII: Synthesis of lambertellin . J. Chem. Soc. C 1970 , 109 – 110 .
  • Keniry , M. A. ; Poulton , G. A. Assignment of quaternary carbon resonances in lambertellin by soft heteronuclear multiple bond correlation . Magn. Reson. Chem. 1991 , 29 , 46 – 48 .
  • Goujon , J. Y. ; Zammattio , F. ; Pagnoncelli , S. ; Boursereau , Y. ; Kirschleger , B. A new and efficient synthesis of substituted 2-hydroxymethyl-2-methyl-2H-chromenes . Synlett 2002 , 322 – 324 .
  • Kabalka , G. W. ; Venkataiah , B. ; Das , B. C. Synthesis of 2H-chromenes in ionic liquid solvents . Synlett 2004 , 2194 – 2196 .
  • Kesteleyn , B. ; De Kimpe , N. ; Van Puyvelde , L. Total synthesis of two naphthoquinone antibiotics, psychorubrin and pentalongin, and their C(1)-substituted alkyl and aryl derivatives . J. Org. Chem. 1999 , 64 , 1173 – 1179 .
  • (a) Wang , X.-H. ; Zhang , X.-H. ; Tu , S.-J. ; Shi , F. ; Zou , X. ; Yan , S. A facile route to the synthesis of 1,4-pyranonaphthoquinone derivatives under microwave irradiation without catalyst. J. Heterocycl. Chem. 2009, 46, 832–836; (b) Yao , C. ; Yu , C. ; Li , T. ; Tu , S. An efficient synthesis of 4H-benzo[g]chromene-5,10-dione derivatives through triethylbenzylammonium chloride–catalyzed multicomponent reaction under solvent-free conditions. Chin. J. Chem. 2009, 27, 1989–1994; (c) Khodeir , M. ; El-Taweel , F. ; Elagamey , A. Polyfunctionally substituted heterocycles: Routes to 4H-naphtho[2,3-b]pyrans, pyridines, and 4H-naphtho[1,2-b]pyrano[2,3-d]pyrimidines. Pharmazie 1992, 47, 486–487; (d) Khurana , J. M. ; Nand , B. ; Saluja , P. DBU: A Highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H benzo[h]chromenes, and 2-amino-4H benzo[g]chromenes in aqueous medium. Tetrahedron 2010, 66, 5637–5641; (e) Shaabani , A. ; Ghadari , R. ; Ghasemi , S. ; Pedarpour , M. ; Rezayan , A. H. ; Sarvary , A. Novel one-pot three- and pseudo-five-component reactions: Synthesis of functionalized benzo[g]- and dihydropyrano[2,3-g]chromene derivatives. J. Comb. Chem. 2009, 11, 956–959.
  • Sheldon , R. A. Selective catalytic synthesis of fine chemicals: Opportunities and trends . J. Mol. Catal. A: Chem. 1996 , 107 , 75 – 83 .
  • (a) Khurana , J. M. ; Kukreja , G. ; Bansal , G. Desulfurization of thioureas, benzimidazoline-2-thiones, and 1,3-dihydro-1,3-diaryle-2-thioxopyrimidine-4,6(2H,5H)-diones with nickel boride at ambient temperature . J. Chem. Soc., Perkin Trans. 1 2002 , 2520 – 2524 ; (b) Khurana , J. M. ; Kukreja , G. Nickel boride–mediated reductive desulfurization of 2-thioxo-4(3H)-quinazolinones: A new synthesis of quinazolin-4(3H)-ones and 2,3-dihydro-4(1H)-quinazolinones . J. Heterocycl. Chem. 2003 , 40 , 677 – 679 ; (c) Khurana , J. M. Agrawal , A. ; Kukreja , G. A novel two-step synthesis of 3,4-dihydro-4-oxo-5H-pyrano[2,3-d]pyrimidines . Heterocycles 2006 , 68 , 1885 – 1889 ; (d) Khurana , J. M. ; Arora , R. ; Satija , S. 7,11-Diaryl-2,4-diazospiro[5.5]undecane-1,5,9-triones: A new series of spiro-heterocycles . Heterocycles 2007 , 71 , 2709 – 2716 ; (e) Khurana , J. M. ; Sharma , V. A novel synthesis of 2-substitued 2H-imidazo[1,5-b]isoquinoline-1,5-diones by in situ desulfurization . Chem. Heterocycl. Comp. 2008 , 44 , 309 – 313 ; (f) Khurana , J. M. ; Kumar , S. Tetrabutylammonium bromide (TBAB): A neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions . Tetrahedron Lett. 2009 , 50 , 4125 – 4127 ; (g) Khurana , J. M. ; Magoo , D. pTSA-catalysed one-pot synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones in ionic liquid and neat conditions . Tetrahedron Lett. 2009 , 50 , 4777 – 4780 ; (h) Khurana , J. M. ; Magoo , D. Efficient one-pot syntheses of 2H-indazolo[2,1-b] phthalazine-triones by catalytic H2SO4 in water–ethanol or ionic liquid . Tetrahedron Lett. 2009 , 50 , 7300 – 7303 .
  • (a) Welton , T. Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 – 2083 ; (b) Wasserscheid , P. ; Keim , W. Ionic liquids: New “solutions” for transition-metal catalysis . Angew. Chem. Int. Ed. 2000 , 39 , 3772 – 3789 ; (c) Welton , T. Ionic liquids in catalysis . Coord. Chem. Rev. 2004 , 248 , 2459 – 2477 .
  • (a) Mi , X. ; Luo , S. ; Cheng , J. P. Ionic liquid–immobilized quinuclidine-catalyzed Morita–Baylis–Hillman reactions . J. Org. Chem. 2005 , 70 , 2338 – 2341 ; (b) Hangarge , R. V. ; Jarikotev , D. V. ; Shingare , M. S. Knoevenagel condensation reactions in an ionic liquid . Green. Chem. 2002 , 4 , 266 – 268 .
  • Ranu , B. C. ; Banerjee , S. Ionic liquid as catalyst and reaction medium: The dramatic influence of task-specific ionic liquid, [bmim]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles . Org. Lett. 2005 , 7 , 3049 – 3052 .
  • (a) Bohnote , P. ; Dias , A. P. ; Papageorgiou , N. ; Kalyanasundaram , K. ; Gratzel , M. Hydrophobic, highly conductive, ambient-temperature molten salts . Inorg. Chem. 1996 , 35 , 1168 – 1178 ; (b) Swarez , P. A. Z. ; De Souza , R. F. ; Dupont , J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes . Polyhedron 1996 , 15 , 1217 – 1219 ; (c) Park , S. ; Kazlauskas , R. J. Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations . J. Org. Chem. 2001 , 66 , 8395 – 8401 .

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.