Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 11
265
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Microwave‐Assisted Solvent‐Free Regiospecific Synthesis of 5‐Alkylidene and 5‐Arylidenehydantoins

, , , , &
Pages 1575-1584 | Received 21 Oct 2005, Published online: 21 Aug 2006

References

  • Gedye , R. , Smith , F. , Westaway , K. , Ali , H. , Baldisera , L. , Laberge , L. and Rousell , J. 1986 . The use of microwave ovens for rapid organic synthesis . Tetrahedron Lett. , 27 : 279 – 282 .
  • Giguere , R. J. , Bray , T. L. , Duncan , S. M. and Majetich , G. 1986 . Application of commercial microwave ovens to organic synthesis . Tetrahedron Lett. , 27 : 4945 – 4948 .
  • Bougrin , K. , ; , Loupy and ASoufiaoui , M. 2005 . Microwave‐assisted solvent‐free heterocyclic synthesis . Photochem. Rev. , 6 : 139 – 167 .
  • Hayes , B. L. 2004 . Recent advances in microwave‐assisted synthesis . Aldrichim. Acta , 37 : 66 – 77 .
  • Loupy , A. 2002 . Microwaves in Organic Synthesis Edited by: Loupy , A. Weinheim : Wiley‐VCH .
  • Atir , A. , Mallouk , S. , Bougrin , K. , Laghzizil , A. and Soufiaoui , M. 2005 . Porous calcium hydroxyapatite efficient catalyst for synthesis of pyrazolines via 1,3‐dipolar cycloaddition under solvent‐free microwave irradiation . Synth. Commun. , 36 : 111 – 120 .
  • Bougrin , K. , Lamiri , M. and Soufiaoui , M. 1998 . Synthèse “one pot” de dérivés isoxazoliniques par activation sonochimique . Tetrahedron Lett. , 39 : 4455 – 4458 .
  • Syassi , B. , Bougrin , K. , Lamiri , M. and Soufiaoui , M. 1998 . Synthèse “One‐pot” de quelques Dérivés Pyrazoliniques et Pyrazoliques en “milieu sec” et sous irradiation micro – onde . New J. Chem. , 22 : 1545 – 1548 .
  • Scholl , S. , Koch , A. , Henning , D. , Kempter , G. and Kleinpeter , E. 1999 . The influence of structure and lipophilicity of hydantoin derivatives on anticonvulsant activity . Struct. Chem. , 10 : 355 – 366 .
  • Hassell , T. M. , Johnston , M. C. and Dudley , K. H. 1980 . Phenytoin‐Induced Teratology and Gingival Pathology Edited by: Hassell , T. M. , Johnston , M. C. and Dudley , K. H. New York : Raven Press .
  • Comber , R. N. , Reynolds , R. C. , Friedrich , J. D. , Manguikian , R. A. , Buckheit , R. W. Jr. , Truss , J. W. , Shannon , W. M. and Secrist , J. A. 1992 . 5,5‐disubstituted hydantoins: syntheses and anti‐HIV activity . J. Med. Chem. , 35 : 3567 – 3572 .
  • Menéndez , J. C. , Diaz , M. P. , Bellver , C. and Söllhuber , M. M. 1992 . Synthesis, anticonvulsant and antihypertensive activity of diastereomeric 9,10‐dimethoxy‐1,3,4,6,7,11b‐hexahydrospiro‐[benzo[a]quinolizin‐2,4′‐imidazolidine]‐2′,5′‐diones . Eur. J. Med. Chem. , 27 : 61 – 66 .
  • Hanessian , S. , Sanceau , J.‐Y. and Chemla , P. 1995 . Synthesis of surrogate structures related to the herbicidal agent hydantocidin . Tetrahedron , 51 : 6669 – 6678 .
  • Purkins , L. , Wood , N. , Ghahramani , P. , Love , E. R. , Eve , M. D. and Fielding , A. 2003 . Coadministration of voriconazole and phenytoin: Pharmacokinetic interaction, safety, and toleration . Br. J. Clin. Pharmacol. , 56 : 37 – 44 .
  • Szymanska , E. , Kiec‐Kononowicz , K. , Bialecka , A. and Kasprowicz , A. 2002 . Antimicrobial activity of 5‐arylidene aromatic derivatives of hydantoin . Il Farmaco. , 57 : 39 – 44 .
  • Zask , A. , Birnberg , G. , Cheung , K. , Kaplan , J. , Niu , C. , Norton , E. , Yamashita , A. , Beyer , C. , Krishnamurthy , G. , Greenberger , L. M. , Loganzo , F. and Ayral‐Kaloustian , S. 2004 . D‐piece modifications of the hemiasterlin analog HTI‐286 produce potent tubulin inhibitors . Bioorg. Med. Chem. Lett. , 14 : 4353 – 4358 .
  • Dundar , B. , Bozdag‐Dundar , O. , Can‐Eke , B. , Coban , T. , Iscan , M. and Buyukbingol , E. 2002 . Synthesis and antioxidative properties of novel thiazolidinedione/imidazolidinedione compounds as retinoids . Pharmazie , 57 : 438 – 441 .
  • Thenmozhiyal , J. C. , Wong , P. T.‐H. and Chui , W.‐K. 2004 . Anticonvulsant activity of phenylmethylenehydantoins: A structure–activity relationship study . J. Med. Chem. , 47 : 1527 – 1535 .
  • Wong , P. T.H. and Tan , S. F. 1989 . Pharmacological profiles of 5‐phenylmethylenehydantoin and its methoxy substituted derivatives . Jpn. J. Pharmacol. , 49 : 309 – 315 .
  • Andreani , A. , Locatelli , A. , Leoni , A. , Morigi , R. , Chiericozzi , M. , Fraccari , A. , Galatulas , I. and Salvatore , G. 1998 . Synthesis and potential coanthracyclinic activity of pyridylmethylene and indolylmethylene lactams . Eur. J. Med. Chem. , 33 : 905 – 909 .
  • Meusel , M. and Guetschow , M. 2004 . Recent developments in hydantoin chemistry . Org. Prep. Proced. Int. , 36 : 391 – 443 .
  • Conway , S. J. , Miller , J. C. , Howson , P. A. , Clark , B. P. and Jane , D. E. 2001 . Synthesis of phenylglycine derivatives as potent and selective antagonists of group III metabotropic glutamate receptors . Bioorg. Med. Chem. Lett. , 11 : 777 – 780 .
  • Monn , J. A. , Valli , M. J. , Massey , S. M. , Hansen , M. M. , Kress , T. J. , Wepsiec , J. P. , Harkness , A. R. , Grutsch , J. L. Jr. , Wright , R. A. , Johnson , B. G. , Andis , S. L. , Kingston , A. , Tomlinson , R. , Lewis , R. , Griffey , K. R. , Tizzano , J. P. and Schoepp , D. D. 1999 . Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)‐2‐aminobicyclo[3.1.0]hexane‐2,6‐dicarboxylic acid (LY354740): Identification of two new potent, selective, and systemically active agonists for group II metabotropic glutamate receptors . J. Med. Chem. , 42 : 1027 – 1040 .
  • Tellier , F. , Acher , F. , Brabet , I. , Pin , J.‐P. and Azerad , R. 1998 . Aminobicyclo[2.2.1.]heptane dicarboxylic acids (ABHD), rigid analogs of ACPD and glutamic acid: Synthesis and pharmacological activity on metabotropic receptors mGluR1 and mGluR2 . Bioorg. Med. Chem. , 6 : 195 – 208 .
  • Monn , J. A. , Valli , M. J. , Massey , S. M. , Wright , R. A. , Salhoff , C. R. , Johnson , B. G. , Howe , T. , Alt , C. A. , Rhodes , G. A. , Robey , R. L. , Griffey , K. R. , Tizzano , J. P. , Kallman , M. J. , Helton , D. R. and Schoepp , D. D. 1997 . Design, synthesis, and pharmacological characterization of (+)‐2‐aminobicyclo[3.1.0]hexane‐2,6‐dicarboxylic acid (LY354740): A potent, selective, and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties . J. Med. Chem. , 40 : 528 – 537 .
  • Aldrich , J. V. , Zheng , Q. and Murray , T. F. 2001 . Dynorphin A analogs containing a conformationally constrained phenylalanine derivative in position 4: Reversal of preferred stereochemistry for opioid receptor affinity and discrimination of kappa vs delta receptors . Chirality , 13 : 125 – 129 .
  • Darula , Z. , Koever , K. E. , Monory , K. , Borsodi , A. , Mako , E. , Ronai , A. , Tourwe , D. , Peter , A. and Toth , G. 2000 . Deltorphin II analogues with 6‐hydroxy‐2‐aminotetralin‐2‐carboxylic acid in position 1 . J. Med. Chem. , 43 : 1359 – 1366 .
  • Smythe , M. L. , Nakaie , C. R. and Marshall , G. R. 1995 . Alpha‐helical versus 310‐helical conformation of alanine‐based peptides in aqueous solution: An electron spin resonance investigation . J. Am. Chem. Soc. , 117 : 10555 – 10562 .
  • Heerding , D. A. , Christmann , L. T. , Clark , T. J. , Holmes , D. J. , Rittenhouse , S. F. , Takata , D. T. and Venslavsky , J. W. 2003 . New benzylidenethiazolidinediones as antibacterial agents . Bioorg. Med. Chem. Lett. , 13 : 3771 – 3773 .
  • Tan , S. F. , Ang , K. P. and Fong , Y. F. 1986 . (Z)‐ and (E)‐5‐Arylmethylenehydantoins: Spectroscopic properties and configuration assignment . J. Chem. Soc., Perkin Trans. 2 , : 1941 – 1944 .
  • Billek , G. 1961 . p‐Hydroxyohenylpyruvic acid . Monatsh. Chem. , 92 : 335 – 342 .
  • Shabica , A. C. , Howe , E. E. , Ziegler , J. B. and Tishler , M. 1946 . Improved syntheses of indole‐3‐aldehyde . J. Am. Chem. Soc. , 68 : 1156 – 1157 .
  • Raap , J. , Nieuwenhuis , S. , Creemers , A. , Hexspoor , S. , Kragl , U. and Lugtenburg , J. 1999 . Synthesis of isotopically labelled L‐phenylalanine and L‐tyrosine . Eur. J. Org. Chem. , : 2609 – 2621 .
  • Ward , H. P. 1952 . Some substituted 5‐benzalhydantoins and 5‐benzylhydantoins . J. Am. Chem. Soc. , 74 : 4212 – 4213 .
  • Henze , H. R. and Allen , G. R. Jr. 1955 . A study of the structure of some derivatives of 5‐(o–nitrobenzylidene)‐hydantoin . J. Am. Chem. Soc. , 77 : 461 – 464 .
  • Jiang , H. , Tu , S. , Miao , C. , Fang , F. , Zhu , S. , Li , T. , Zou , X. and Zhang , X. 2004 . A new synthesis method of 5‐arylidenehydantoin and the crystal structure . Huaxue Tongbao , 67 : w58/51 – w58/54 .
  • Loupy , A. 2004 . Solvent‐free microwave organic synthesis as an efficient procedure for green chemistry . Comptes Rendus Chimie , 7 : 103 – 112 .
  • Varma , R. S. 2001 . Solvent‐free accelerated organic syntheses using microwaves . Pure Appl. Chem. , 73 : 193 – 198 .
  • Varma , R. S. 1999 . Solvent‐free organic syntheses: Using supported reagents and microwave irradiation . Green Chem. , 1 : 43 – 55 .
  • Loupy , A. , Petit , A. , Hamelin , J. , Texier‐Boullet , F. , Jacquault , P. and Mathé , D. 1998 . New solvent‐free organic synthesis using focused microwaves . Synthesis , : 1213 – 1234 .
  • Gasgnier , M. , Szwarc , H. , Petit , A. , Nahmias , J. and Loupy , A. 2001 . Alkylation reactions of potassium carboxylates supported on alumina: Comparison between ball‐milling, impregnation and dispersion procedures . J. Chem. Soc., Perkin Trans. 2 , : 1233 – 1238 .
  • Bram , G. , Loupy , A. , Majdoub , M. , Gutierrez , E. and Ruiz‐Hitzky , E. 1990 . Alkylation of potassium acetate in “dry media” thermal activation in commercial microwave ovens . Tetrahedron , 46 : 5167 – 5176 .
  • Villemin , D. and Thibault‐Starzyk , F. 1991 . Domestic microwave ovens in the laboratory . J. Chem. Educ. , 68 : 346
  • Kleinpeter , E. 1997 . The structure of hydantoins in solution and in the solid state . Struct. Chem. , 8 : 161 – 173 .
  • Bougrin , K. , Soufiaoui , M. , Loupy , A. and Jacquault , P. 1995 . Addition Dipolaire1,3 de la Diphénylnitrilimine sur Quelques Dipolarophiles en “milieu sec” sous Micro‐ondes . New J. Chem. , 19 : 213 – 219 .
  • Loupy , A. , Bram , G. and Sansoulet , J. 1992 . Anionic activation in solvent‐free heterogeneous media, utilization of microwaves ovens . New J. Chem. , 16 : 233 – 242 .
  • Starks , C. M. 1971 . Phase‐transfer catalysis, I: Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts . J. Am. Chem. Soc. , 93 : 195 – 199 .
  • Gabriel , C. , Gabriel , S. , Grant , E. H. , Grant , E. H. and Halstead , B. S. 1998 . J.; Mingos, D.M.P. Dielectric parameters relevant to microwave dielectric heating . Chem. Soc. Rev. , 27 : 213 – 224 .

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.