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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 21
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Original Articles

Facile and Highly Efficient Procedure for the Synthesis of Triazolyl Methoxyphenyl 1,8-Dioxo-decahydroacridines via One-Pot, Pseudo-Five-Component Reaction

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Pages 3117-3127 | Received 14 Mar 2011, Published online: 17 Aug 2012

REFERENCES

  • (a) Moses , J. E. ; Moorhouse , A. D. The growing applications of click chemistry . Chem. Soc. Rev. 2007 , 36 , 1249 – 1262 ; (b) Lutz , J. F. 1,3-Dipolar cycloadditions of azides and alkynes: A universal ligation tool in polymer and materials science . Angew. Chem. Int. Ed. 2007 , 46 , 1018 – 1025 .
  • Kolb , H. C. ; Finn , M. G. ; Sharpless , K. B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2004–2021.
  • Bock , V. D. ; Hiemstra , H. ; Van Maarseveen , J. H. CuI-catalyzed alkyne-azide “click” cycloadditions from a mechanistic and synthetic perspective . Eur. J. Org. Chem. 2006 , 1 , 51 – 68 .
  • Tornøe , C. W. ; Christensen , C. ; Meldal , M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides . J. Org. Chem. 2002 , 67 , 3057 – 3064 .
  • Rostovtsev , V. V. ; Green , L. G. ; Fokin , V. V. ; Sharpless , K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes . Angew. Chem., Int. Ed. 2002 , 41 , 2596 – 2599 .
  • Albert , A. The Acridines, ed. , 2nd ; Edward Arnold Ltd : London , 1996 .
  • Huang , X. ; Zhang , T. Cascade nucleophilic addition–cyclic Michael addition of arynes and phenols/anilines bearing ortho α,β-unsaturated groups: Facile synthesis of 9-functionalized xanthenes/acridines . J. Org. Chem. 2010 , 75 , 506 – 509 .
  • Fukuzumi , S. ; Okamoto , K. ; Tokuda , Y. ; Gros , C. P. ; Guilard , R. Dehydrogenation versus oxygenation in two-electron and four-electron reduction of dioxygen by 9-alky-10-methyl-9,10-dihydroacridines catalyzed by monomeric cobalt porphyrins and cofacial dicobalt porphyrins in the presence of perchloric acid . J. Am. Chem. Soc. 2004 , 126 , 17059 – 17066 .
  • Santelli-Rouvier , C. ; Pradines , B. ; Berthelot , M. ; Parzy , D. ; Barbe , J. Arylsulfonyl acridinyl derivatives acting on Plasmodium falciparum . Eur. J. Med. Chem. 2004 , 39 , 735 – 744 .
  • Su , T.-L. ; Lin , Y.-W. ; Chou , T.-C. ; Zhang , X. ; Bacherikov , V. A. ; Chen , C.-H. ; Liu , L. F. ; Tsai , T.-J. Potent antitumor 9-anilinoacridines and acridines bearing an alkylating N-mustard residue on the acridine chromophore: Synthesis and biological activity . J. Med. Chem. 2006 , 49 , 3710 – 3718 .
  • May , B. C. H. ; Witkop , J. ; Sherrill , J. ; Anderson , M. O. ; Madrid , P. B. ; Zorn , J. A. ; Prusiner , S. B. ; Cohen , F. E. ; Guy , R. K. Structure–activity relationship study of 9-aminoacridine compounds in scrapie-infected neuroblastoma cells . Bioorg. Med. Chem. Lett. 2006 , 16 , 4913 – 4916 .
  • Fang , L. ; Appenroth , D. ; Decker , M. ; Kiehntopf , M. ; Roegler , C. ; Deufel , T. ; Fleck , C. ; Peng , S. ; Zhang , Y. ; Lehmann , J. Synthesis and biological evaluation of NO-donor-tacrine hybrids as hepatoprotective anti-Alzheimer drug candidates . J. Med. Chem. 2008 , 51 , 713 – 716 .
  • Gamage , S. A. ; Figgitt , D. P. ; Wojcik , S. J. ; Ralph , R. K. ; Ransijn , A. ; Mauel , J. ; Yardley , V. ; Snowdon , D. ; Croft , S. L. ; Denny , W. A. Structure–activity relationships for the antileishmanial and antitrypanosomal activities of 1′-substituted 9-anilinoacridines . J. Med. Chem. 1997 , 40 , 2634 – 2642 .
  • Zang , H. ; Zhang , Y. ; Zang , Y. ; Cheng , B.-W. An efficient ultrasound-promoted method for the one-pot synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives . Ultrason. Sonochem. 2010 , 17 , 495 – 499 .
  • Wang , X.-S. ; Zhang , M.-M. ; Zeng , Z.-S. ; Shi , D.-Q. ; Tu , S.-J. ; X.-Y. ; Zong , Z.-M. A simple and clean procedure for the synthesis of polyhydroacridine and quinoline derivatives: Reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium . Tetrahedron Lett. 2005 , 46 , 7169 – 7173 .
  • Nadaraj , V. ; Thamarai Selvi , S. ; Mohan , S. Microwave-induced synthesis and anti-microbial activities of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives . Eur. J. Med. Chem. 2009 , 44 , 976 – 980 .
  • (a) Dabiri , M. ; Baghbanzadeh , M. ; Arzroomchilar , E. 1-Methylimidazolium triflouroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines. Catal. Commun. 2008, 9, 939–942; (b) Dabiri , M. ; Bahramnejad , M. ; Baghbanzadeh , M. Ammonium salt–catalyzed multicomponent transformation: Simple route to functionalized spirochromenes and spiroacridines. Tetrahedron 2009, 65, 9443–9447; (c) Dabiri , M. ; Bahramnejad , M. ; Bashiribod , S. TFA-catalyzed multicomponent reaction: Direct, mild, and efficient procedure for the synthesis of 1,2-dihydroquinazoline derivatives. Mol. Divers. 2010, 14, 507–512.
  • Dabiri , M. ; Salehi , P. ; Bahramnejad , M. ; Sherafat , F. Synthesis of diheterocyclic compounds based on triazolyl methoxy phenylquinazolines via a one-pot four-component click reaction . J. Comb. Chem. 2010 , 12 , 638 – 642 .
  • (a) Karaev , S. F. ; Garaeva , S. V. Prop-2-ynyl ethers . Russ. Chem. Rev. 1980 , 49 , 865 – 879 ; (b) Frixa , C. ; Mahon , M. F. Thompson , A. S. ; Threadgill , M. D. Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapy . Org. Biomol. Chem. 2003 , 1 , 306 – 317 .
  • (a) Bräse , S. ; Gil , C. ; Knepper , K. ; Zimmermann , V. Organic azides: An exploding diversity of a unique class of compounds . Angew. Chem., Int. Ed. 2005 , 44 , 5188 – 5240 ; (b) Scriven , E. F. V. ; Turnbull , K. Azides: Their preparation and synthetic uses . Chem. Rev. 1988 , 88 , 297 – 368 .

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