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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 2
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Original Articles

First Highly Efficient Synthesis of bis(Arylmethylidene)pyranones Mediated by Lithium Perchlorate

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Pages 199-206 | Received 26 Jun 2005, Published online: 15 Aug 2006

References

  • Hathaway , B. A. 1987 . An aldol condensation experiment using a number of aldehydes and ketones . J. Chem. Educ. , 64 : 367 – 368 .
  • Zheng , M. , Wang , L. , Shao , J. and Zhong , Q. 1997 . A facile synthesis of α‐α′‐bis(substituted benzylidene)cycloalkanones catalyzed by bis(p‐ethoxyphenyl)telluroxide (BMPTO) under microwave irradiation . Synth. Commun. , 27 : 351 – 354 .
  • Iranpoor , N. and Kazemi , E. 1998 . RuCl3 catalyses aldol condensations of aldehydes and ketones . Tetrahedron , 54 : 9475 – 9480 .
  • Nakano , T. and Migita , T. 1993 . A convenient synthesis of α,α′‐bis(substituted benzylidene)cycloalkanones . Chem. Lett. , 22 : 2157 – 2158 .
  • Wang , J. , Kang , L. , Hu , Y. and Wei , B. 2002 . Synthesis of bis(substituted benzylidene)cycloalkanone using supported reagents and microwave irradiation . Synth. Commun. , 32 : 1691 – 1696 .
  • Li , J. , Yang , W. , Chen , G. and Li , T. 2003 . A facile synthesis of α,α′‐bis(substituted benzylidene)cycloalkanones catalyzed by KF/Al2O3 under ultrasound irradiation . Synth. Commun. , 33 : 2619 – 2625 .
  • Wang , L. , Sheng , J. , Tian , H. , Han , J. , Fan , Z. and Qian , C. 2004 . A convenient synthesis of α,α′‐bis(substituted benzylidene)cycloalkanones catalyzed by Yb(OTf)3 under solvent‐free conditions . Synthesis , : 3060 – 3064 .
  • Sabitha , G. , Reddy , K. K. , Reddy , K. B. and Yadav , J. S. 2004 . Iodotrimethylsilane‐mediated cross‐aldol condensation: A facile synthesis of α,α′‐bis(substituted benzylidene)cycloalkanones . Synthesis , : 263 – 266 .
  • Iranpoor , N. , Zeynizadeh , B. and Aghapour , A. 1999 . Aldol condensation of cycloalkanones with aromatic aldehydes catalysed with TiCl3(SO3CF3) . J. Chem. Res. , : 554 – 555 .
  • Zhu , Y. and Pan , Y. 2004 . A new Lewis acid system palladium/TMSCI for catalytic aldol condensation of aldehydes with ketones . Chem. Lett. , 33 : 668 – 669 .
  • Zheng , X. and Zhang , Y. 2003 . SmI3‐catalyzed condensation of aliphatic cycloketones and aldehydes in ionic liquid . Synth. Commun. , 33 : 161 – 165 .
  • Hu , X. , Fan , X. , Zhang , X. and Wang , J. 2004 . InCl3 · 4H2O/TMSCI‐catalysed aldol reaction of aromatic aldehydes with cycloalkanones in ionic liquid medium . J. Chem. Res. , : 684 – 686 .
  • Zhang , X. , Fan , X. , Niu , H. and Wang , J. 2003 . An ionic liquid as a recyclable medium for the green preparation of α,α′‐bis(substituted benzylidene)cycloalkanones catalyzed by FeCl3 · 6H2O . Green Chem. , 5 : 267 – 269 .
  • Zacuto , M. J. and Cai , D. 2005 . α‐Hydroxylation of carbonyls using iodine . Tetrahedron Lett. , 46 : 447 – 450 .
  • Rovnyak , G. , Shu , V. and Schwartz , J. 1981 . Tricyclic thiazolo[3,2‐a]thiapyrano[4,3‐d]pyrimidines and related analogs as potential anti‐inflammatory agents . J. Heterocycl. Chem. , 18 : 327 – 331 .
  • Leonard , N. J. and Choudhury , D. 1957 . γ‐Pyrones by isomerization. Substituted 3,5‐dibenzyl‐4H‐pyran‐4‐one . J. Am. Chem. Soc. , 79 : 156 – 160 .
  • Pirelahi , H. , Parchamazad , I. , Abaee , M. S. and Sheikhebrahimi , S. 1991 . Photochromism study in some 4‐thiopyran derivatives . Phosphorus, Sulfur Silicon Relat. Elem. , 59 : 251 – 254 .
  • Pirelahi , H. , Hashtroodi , M. S. , Abaee , M. S. and Shariati , Y. R. 1994 . Novel photoisomerization of some 2,4,4,6‐tetrasubstituted 4H‐thiopyran to isomeric 2H‐thiopyrans . J. Photochem. Photobiol. A: Chem. , 81 : 21 – 25 .
  • Mojtahedi , M. M. , Jalali , M. R. and Bolourtchian , M. 2006 . A facile synthesis of pyrano[2,3‐c]pyrazol‐6‐one derivatives under microwave irradiation in solvent‐free conditions . Synth. Commun. , 36 in press
  • Zhou , J. F. 2003 . One‐step synthesis of pyridine and 4‐H‐pyran derivatives from bisarylidenecyclohexanone and malonitrile under microwave irradiation . Synth. Commun. , 33 : 99 – 103 .
  • Marco , J. L. , Martin , N. , Grau , A. M. , Seoane , C. , Albert , A. and Cano , F. H. 1994 . Development of methods for the synthesis of chiral, highly functionalized 2‐amino‐4‐aryl‐4H‐pyrans . Tetrahedron , 50 : 3509 – 3528 .
  • Albert , D. A. , Cano , F. H. , Ramos , A. , Rodriguez , M. , Segura , J. L. and Soane , C. J. 1997 . A study on the scope of the photochemical ring contraction of substituted 2‐amino‐3‐cyano‐4H‐pyrans to cyclobutenes: Crystal structure of 3‐carbamoyl‐3‐cyano‐1‐ethoxycarbonyl‐4‐isopropyl‐2‐phenylcyclobutene . J. Chem. Soc., Perkin Trans. 1 , : 3401 – 3406 .
  • Hunt , K. W. and Grieco , P. A. 2001 . Oxabicyclo[3,2,1]octenes in organic synthesis—direct ring opening of oxabicyclo[3,2,1] systems employing silyl ketene acetals in concentrated solutions of lithium perchlorate–diethyl ether; application to the synthesis of C(19)–C(27) fragments of rifamycin . S. Org. Lett. , 3 : 481 – 484 .
  • Grieco , P. A. and Kaufman , M. D. 1999 . Construction of carbocyclic arrays containing nitrogen via intramolecular imino Diels–Alder reaction in polar media. A comparative study: 5.0 M lithium perchlorate–diethyl ether versus water . J. Org. Chem. , 64 : 6041 – 6048 .
  • Grieco , P. A. , Clark , J. D. and Jagoe , C. T. 1991 . [1,3] Sigmatropic rearrangement of allyl vinyl ethers at ambient temperature in 3.0 M lithium perchlorate–diethyl ether . J. Am. Chem. Soc. , 113 : 5488 – 5489 .
  • Forman , M. A. and Dailey , W. P. 1991 . The lithium perchlorate–diethyl ether rate acceleration of the Diels–Alder reaction: Lewis acid catalysis by lithium ion . J. Am. Chem. Soc. , 113 : 2761 – 2762 .
  • Azizi , N. and Saidi , M. R. 2004 . Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent‐free and neutral conditions . Organometallics , 23 : 1457 – 1458 .
  • Mojtahedi , M. M. , Saidi , M. R. , Shirzi , J. S. and Bolourtchian , M. 2001 . Ultrasound accelerated reductive coupling of imine or iminium ion generated in 5 M lithium perchlorate solution by lithium metal . Synth. Commun. , 31 : 3587 – 3592 .
  • Saidi , M. R. , Javanshir , S. and Mojtahedi , M. M. 1999 . Lithium perchlorate–mediated three‐component reaction for the preparation of primary amines . J. Chem. Res. , : 330 – 331 .
  • Saidi , R. , Mojtahedi , M. M. and Bolourtchian , M. 1997 . A simple three‐component reaction for the preparation of silylated primary amines . Tetrahedron Lett. , 38 : 8071 – 8072 .
  • Naimi‐Jamal , M. R. , Mojtahedi , M. M. , Ipaktschi , J. and Saidi , M. R. 1999 . Aminosilylation of aldehydes mediated by lithium perchlorate: Novel method for synthesis of α‐silylamines . J. Chem. Soc., Perkin Trans. 1 , : 3709 – 3711 .

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