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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

Synthesis of 1‐Indanones via Intramolecular Cyclodehydration of 3‐Arylpropionic Acids Catalyzed by Heteropoly Acid as Heterogeneous Catalyst

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Pages 2171-2177 | Received 20 Sep 2006, Published online: 03 Jul 2007

References

  • Sugimoto , H. 1999 . Structure–activity relationships of acetylcholinesterase inhibitors: Donepezil hydrochloride for the treatment al Alzheimer's disease . Pure. Appl. Chem. , 71 ( 11 ) : 2031 – 2037 .
  • Schumann , H. , Stenzel , O. , Girgsdies , F. and Halterman , R. L. 2001 . Synthesis and characterization of (‐)‐1‐menthyl‐4,7‐dimethylindene and its main group metal compounds with lithium, sodium, potassium, and tin . Organometallics , 20 ( 9 ) : 1743 – 1751 .
  • Sato , Y. and Takimoto , J. 1998 . Preparation of truxenes as mesogens for discotic liquid crystal . Jpn. Kokai Tokkyo Koho , JP 10324648, 19981208; Appl. No: JP19970148620; 19970522
  • Cui , D. M. , Zhang , C. , Kawamura , M. and Shimada , S. 2004 . Synthesis of 1‐indanones by intramolecular Friedel–Crafts reaction of 3‐arylpropionic acids catalyzed by Tb(OTf)3 . Tetrahedron Lett. , 45 ( 8 ) : 1741 – 1745 .
  • Khalaf , A. A. , Abdel‐Wahab , A. A. , El‐Khawaga , A. M. and El‐Zohry , M. F. 1984 . Modern Friedel–Crafts chemistry, XIII: Intra‐ and intermolecular cyclization of some carbonyl derivatives under Friedel–Crafts conditions . Bull. Soc. Chim. Fran. , 7–8 : 285 – 291 .
  • Smonou , I. and Orfanopoulos , M. 1990 . Convenient synthetic sequence for the preparation of indanones . Synth. Comm. , 20 ( 9 ) : 1387 – 1397 .
  • Hendrickson , J. B. and Hussoin , M. S. 1989 . Reactions of carboxylic acids with phosphonium anhydrides . J. Org. Chem. , 54 ( 5 ) : 1144 – 1149 .
  • Bobbitt , J. M. , Katritzky , A. R. , Kennewell , P. D. and Snarey , M. 1968 . Steric requirements of sp2‐hybridized lone electron pairs, I: The conformations of 2‐(pyridylmethylene) indan‐1‐ones . J. Chem. Soc. B , 5 : 550 – 554 .
  • Fieser , L. F. and Hershberg , E. B. 1939 . Inter‐ and intra‐molecular acylations with hydrogen fluoride . J. Am. Chem. Soc. , 61 : 1272
  • Guy , A. , Guette , J. P. and Lang , G. 1980 . Utilization of polyphosphoric acid in the presence of a cosolvent . Synth. , 3 : 222 – 223 .
  • Imaki , S. , Takuma , J. and Endo , K. 1991 . Preparation of cyclic ketones . Jpn. Kokai Tokkyo Koho , JP 03279343, 19911210; Appl. No: JP19900212583; 19900810
  • Bruce , D. B. , Sorrie , A. J. S. and Thomson , R. H. 1953 . Reactions in fused aluminum chloride–sodium chloride . J. Chem. Soc. , : 2403
  • Wade , L. G. , Acker , K. J. , Earl , R. A. and Osteryoung , R. A. 1979 . Cyclodehydration reactions using molten sodium tetrachloroaluminate . J. Org. Chem. , 44 ( 21 ) : 3724 – 3725 .
  • El‐Sayrafi , S. and Rayyan , S. 2001 . Intramolecular acylation of aryl‐ and aroyl‐aliphatic acids by the action of pyrophosphoryl chloride and phosphorus oxychloride . Molecules , 6 ( 3 ) : 279 – 286 .
  • Sartori , G. and Maggi , R. 2006 . Use of solid catalysts in Friedel–Crafts acylation reactions . Chem. Rev. , 106 ( 3 ) : 1077 – 1104 .
  • Wilson , K. and Clark , J. H. 2000 . Solid acids and their use as environmentally friendly catalysts in organic synthesis . Pure. Appl. Chem. , 72 ( 7 ) : 1313 – 1319 .
  • Badri , R. and Tavakoli , L. 2003 . Friedel–Crafts acylation of aryl‐substituted carboxylic acids catalyzed by zeolite . J. Incl. Phenom. Macrocycl. Chem. , 45 ( 1–2 ) : 41 – 43 .
  • Kozhevnikov , I. V. 2003 . Friedel–Crafts acylation and related reactions catalyzed by heteropoly acids . Appl. Catal. A , 256 ( 1–2 ) : 3 – 18 .
  • Timofeeva , M. N. 2003 . Acid catalysis by heteropoly acids . Appl. Catal. A , 256 ( 1–2 ) : 19 – 35 .
  • Kozhevnikov , I. V. 1998 . Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid‐phase reactions . Chem. Rev. , 98 ( 1 ) : 171 – 198 .
  • Lan , K. , Shan , Z. and Fan , S. 2006 . Synthesis of spirobiindanes via bis‐cyclization reaction of the 1,5‐diaryl‐3‐pentanones catalyzed by heteropoly acids . Tetrahedron Lett. , 47 ( 26 ) : 4343 – 4345 .
  • Stock , L. M. and Brown , H. C. 1963 . A quantitative treatment of directive effects in aromatic substitution . Adv. Phys. Org. Chem. , 1 : 35 – 154 .
  • Stock , L. M. and Brown , H. C. 1962 . Directive effects in aromatic substitution, LIV: An examination of the applicability of the selectivity relationship to the electrophilic substitution reactions of the halobenzenes . J. Am. Chem. Soc. , 84 : 1668 – 1673 .

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