Reactivity of Unsaturated 5(4H)-Oxazolones with Hg(II) Acetate: Synthesis of Methyl N-Benzoylamino-3-arylacrylates

REFERENCES

• Cativiela , C. ; Díaz-de-Villegas , M. D. The Chemistry of Heterocyclic Compounds ; Wiley : New York ; D. C. Palmer (Ed.); 2004 ; vol. 60 , pp. 129 – 330 .
   Google Scholar
• Liang , J. ; Ruble , J. C. ; Fu , G. C. Dynamic kinetic resolutions catalyzed by a planar-chiral derivative of DMAP: Enantioselective synthesis of protected α-amino acids from racemic azlactones. J. Org. Chem. 1998, 63, 3154–3155.
   Web of Science ®Google Scholar
• Hoshina , H. ; Tsuru , H. ; Kubo , K. ; Igarashi , T. ; Sakurai , T. Formation of isoquinoline derivatives by the irradiation of N-acetyl-α-dehydrophenylalanine ethyl ester and its derivatives . Heterocycles 2000 , 53 , 2261 – 2274 .
   Web of Science ®Google Scholar
• Keith , D. D. ; Weigele , M. Butenoic acid derivatives. U.S. Patent 4216008, 1980; Chem. Abstr. 1981, 94, 16083.
   Google Scholar
• Bakos , J. ; Gebhardt , I. ; Lukacs , L. ; Kiraly , J. ; Bihari , F. ; Heil , B. ; Durko , M. ; Radvany , B. ; Boros , P. ; Eifert , G. Preparation of acrylic acid derivatives as herbicides. Hungarian Patent HU 47203, 1989; Chem. Abstr. 1991, 114, 116927.
   Google Scholar
• Slouka , J. Preparation of 2-acetylamino-3-[1-phenyl-3-(4-chlorophenyl)-4-pyrazolyl]acrylic acid as an intermediate for lonazolac. Czechoslovakian Patent CS 267956, 1990; Chem. Abstr. 1991, 114, 185493.
   Google Scholar
• Jursic , B. S. ; Sagiraju , S. ; Ancalade , D. K. ; Clark , T. ; Stevens , E. D. Practical preparation of Z-α-(N-acetylamino)- and Z-α-(N-benzoylamino)-α,β-unsaturated acids . Synthetic Commun. 2007 , 37 , 1709 – 1714 .
   Web of Science ®Google Scholar
• Gagey , N. ; Emond , M. ; Neveu , P. ; Benbrahim , C. ; Goetz , B. ; Aujard , I. ; Baudin , J.-B. ; Jullien , L. Alcohol uncaging with fluorescence reporting: Evaluation of o-acetoxyphenyl methyloxazolone precursors . Org. Lett. 2008 , 10 , 2341 – 2344 .
   PubMed Web of Science ®Google Scholar
• (a) Rao , Y. S. ; Filler , R. Geometric isomers of 2-aryl(aralkyl)-4-arylidene(alkylidene)-5(4H)-oxazolones . Synthesis 1975 , 749 – 764 ; (b) Rzeszotarska , B. ; Karolak-Wojciechowska , J. ; Broda , M. A. ; Galdecki , Z. ; Trzezwinska , B. ; Koziol , A. E. Conformational investigation of α,β-dehydropeptides. Part VI. Molecular and crystal structure of benzyloxycarbonylglycyl-(Z)-dehydrophenylalanine . Int. J. Pept. Protein Res. 1994 , 44 , 313 – 319 .
   Google Scholar
• Maekawa , K. ; Hishikawa , N. ; Kubo , K. ; Igarashi , T. ; Sakurai , T. Preferential formation of cis-4,5-dihydrooxazole derivatives via photoinduced electron transfer-initiated cyclization of N-acyl-α-dehydroarylalanine alkyl esters . Tetrahedron 2007 , 63 , 11267 – 11281 .
   Web of Science ®Google Scholar
• Shabana , R. ; Sidky , M. M. ; El-Kateb , A. A. ; Soliman , F. M. Studies on organophosphorus compounds. Part IX. The action of di-, and trialkyl phosphites and thio acids on some enamino lactones . Phosphorus Sulfur 1987 , 34 , 57 – 61 .
   Web of Science ®Google Scholar
• Lee , S. ; Jung , S. Cyclosophoraose as a catalytic carbohydrate for methanolysis . Carbohyd. Res. 2004 , 339 , 461 – 468 .
   PubMed Web of Science ®Google Scholar
• Rao , C. C. ; Lalitha , N. A new methodology for the synthesis of N-acylaminocinnamates and amides from azlactones . Indian J. Chem., Sect. B 1994 , 33 , 3 .
   Google Scholar
• Roiban , D. ; Serrano , E. ; Soler , T. ; Grosu , I. ; Cativiela , C. ; Urriolabeitia , E. P. Unexpected [2 + 2] C-C bond coupling due to photocycloaddition on orthopalladated (Z)-2-aryl-4-arylidene-5(4H)-oxazolones . Chem. Commun. 2009 , 4681 – 4683 .
   PubMed Web of Science ®Google Scholar
• Roiban , G. D. ; Serrano , E. ; Soler , T. ; Contel , M. ; Grosu , I. ; Cativiela , C. ; Urriolabeitia , E. P. Ortho-palladation of (Z)-2-aryl-4-arylidene-5(4H)-oxazolones . Organometallics 2010 , 29 , 1428 – 1435 .
   Web of Science ®Google Scholar
• (a) Constable , E. C. ; Leese , T. A. ; Tocher , D. A. Polynuclear intermediates in the synthesis of cyclometallated complexes; The crystal and molecular structure of (2-pyridylphenyl)mercury(II) chloride tetramer. J. Chem. Soc., Chem. Commun. 1989, 570–571; (b) Clark , A. M. ; Rickard , C. E. F. ; Roper , W. R. ; Wright , L. J. Electrophilic substitution reactions at the phenyl ring of the chelated 2-(2′-pyridyl)phenyl ligand bound to ruthenium(II) or osmium(II). Organometallics 1999, 18, 2813–2820; (c) Parish , R. V. ; Wright , J. P. ; Pritchard , R. G. Mercury(II) and gold(III) derivatives of 2-phenyl pyridines and 2-phenyl-4-(methylcarboxylato)quinoline. J. Organomet. Chem. 2000, 596, 165–176; (d) Clark , A. M. ; Rickard , C. E. F. ; Roper , W. R. ; Wright , L. J. Bromination and nitration reactions of metallated (Ru and Os) multiaromatic ligands and crystal structures of selected products. J. Organomet. Chem. 2000, 598, 262–275.
   Google Scholar
• Gabbaï Melaimi , F. P. ; Burress , C. N. ; Melaimi , M.-A. ; Taylor , T. J. Comprehensive Organometallic Chemistry III ; R. H. Crabtree ; D. M. P. Mingos (Eds.); Elsevier : Amsterdam , U.K. ; 2007 ; vol. 2 , pp. 419 – 474 .
   Google Scholar
• (a) Urriolabeitia , E. P. Palladacycles: Synthesis, Characterization and Applications ; J. Dupont ; M. Pfeffer (Eds.); Wiley : Weinheim , 2008 , pp. 35 – 67 ; (b) Soro, B.; Stoccoro, S.; Minghetti, G.; Zucca, A.; Cinellu, M. A.; Gladiali, S.; Manassero, M.; Sansoni, M. Synthesis of the first C-2 cyclopalladated derivatives of 1,3-bis(2-pyridyl)benzene. Crystal structures of [Hg(N-C-N)Cl], [Pd(N-C-N)Cl], and [Pd2(N-C-N)2(µ-OAc)]2[Hg2Cl6]. Catalytic activity in the Heck reaction. Organometallics 2005, 24, 53–61.
   Google Scholar
• Phillips , I. G. ; Steel , P. J. Cyclometallated compounds : VIII. Double cyclopalladation of diacetylbenzene dioximes and 1,5-bis(dimethylamino)naphthalene . J. Organomet. Chem. 1991 , 410 , 247 – 255 .
   Web of Science ®Google Scholar
• Vicente , J. ; Abad , J.-A. ; Stiakaki , M.-A. ; Jones , P. G. Palladium-assisted rearrangement of HC(O)C6H2(OMe)3-3,4,5 to HC(O)C6H2(OMe)3-2,3,4. X-Ray structures of [PdR(PPh3)(bipy)](CF3SO3)[R=C6H(CHO)-6,(OMe)3-2,3,4 and C6H(CHO)-2,(OMe)3-3,4,5; bipy˭2,2′-bipyridyl] . J. Chem. Soc., Chem. Commun. 1991 , 137 – 139 .
   Google Scholar
• Kumar , K. ; Phelps , D. J. ; Carey , P. R. Resonance Raman labels: Spectroscopic studies on cis- and trans-4-benzylidene-2-phenyl-▵2-oxazolin-5-one and an isotopically substituted analog . Can. J. Chem. 1978 , 56 , 232 – 239 .
   Web of Science ®Google Scholar
• (a) Venkataratnam , R. V. ; Suryakumari , A. Configurational assignment to geometric isomers of 2-phenyl-4-(3-phenyl-2-propenylidene)-5(4H)-oxazolone . Indian J. Chem, Sect. B 1988 , 27 , 832 – 833 ; (b) Prokof′ev , E. P. ; Karpeiskaya , E. I. The proton coupled carbon-13 NMR direct determination of Z-, E-configuration of 4-benzylidene-2-phenyl(methyl)-▵2-oxazolin-5-ones and products of their solvolysis . Tetrahedron Lett. 1979 , 737 – 740 ; (c) Cativiela , C. ; Sanchez-Ferrando , F. Measurement of long-range heteronuclear selective carbon-13 {proton} NOE enhancements: 4-(α-arylethylidene)-2-phenyl-5(4H)-oxazolones . Magn. Reson. Chem. 1985 , 23 , 1072 – 1075 .
   Google Scholar
• (a) Kavrakova , I. ; Koleva , V. ; Kurtev , B. On the relative chromatographic mobility of Z- and E-4-arylidene-2-phenyl-5-oxazolones . Dokl. Bolg. Akad. Nauk 1984 , 37 , 1495 – 1496 ; Chem. Abstr. 1985 , 103 , 37396 ; (b) Palamareva , M. ; Kavrukova , I. Microcomputer aided choice of mobile phases for thin-layer chromatographic separation of some E- and Z-oxazolones and related cinnamates on silica . Izv. Khim. 1988 , 21 , 218 – 225 ; Chem. Abstr. 1989 , 111 , 247239 ; (c) Palamareva , M. ; Kurtev , B. ; Kavrakova , I. Chromatographic behavior of diastereoisomers. X. Thin-layer chromatographic retentions on silica of some (E)- and (Z)-oxazolones and related cinnamates as a function of mobile phase effects or Hammett constants . J. Chromatogr. 1991 , 545 , 161 – 175 .
   Google Scholar
• (a) Haasbroek , P. P. ; Oliver , D. W. ; Carpy , A. J. M. Evidence of the structure of 4-(4′-acetoxybenzylidene)-2-methyl-5-oxazolone and its phenylpropenoic acid derivatives . J. Mol. Struct. 2003 , 648 , 61 – 67 ; (b) Busetti , V. ; Mayoral , J. A. ; Cativiela , C. ; Diaz de Villegas , M. D. ; Ajo , D. Crystal structure of cyclic dehydroaminoacid derivatives. I. Tetrasubstituted (Z)-5(4H)-oxazolones . Z. Kristallogr. 1989 , 189 , 65 – 76 .
   Web of Science ®Google Scholar
• (a) King , S. W. ; Riordan , J. M. ; Holt , E. M. ; Stammer , C. H. Synthesis of racemic (E)- and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid: (E)- and (Z)-cyclopropylphenylalanine . J. Org. Chem. 1982 , 47 , 3270 – 3273 ; (b) Hamidian , H. ; Tikdari , A. M. Novel synthesis of unsaturated 5(4H)-oxazolone derivatives with using palladium(II) acetate as a catalyst and microwave irradiation in solvent-free condition . Heterocycl. Commun. 2006 , 12 , 29 – 34 .
   Web of Science ®Google Scholar
• Pines , S. H. ; Kozlowski , M. A. ; Karady , S. Mechanism and stereochemical considerations in the reaction of some arylserine derivatives with thionyl chloride. J. Org. Chem. 1969, 34, 1621–1627.
   Web of Science ®Google Scholar
• Mesaik , M. A. ; Rahat , S. ; Khan , K. M. ; Zia-Ullah ; Choudhary , M. I. ; Murad , S. ; Ismail , Z. ; Atta-ur-Rahman ; Ahmad , A. Synthesis and immunomodulatory properties of selected oxazolone derivatives . Bioorg. & Med. Chem. 2004 , 12 , 2049 – 2057 .
   PubMed Web of Science ®Google Scholar
• (a) Cativiela , C. ; Diaz de Villegas , M. D. ; Melendez , E. On the synthesis of geometric isomers of 2-methyl (or phenyl)-4-[α-arylethylidene]-5(4H)-oxazolones . J. Heterocycl. Chem. 1985 , 22 , 1655 – 1657 ; (b) Kidwai , M. ; Sapra , P. ; Bhushan , K. R. ; Misra , P. Microwave-assisted solid-support synthesis of pyrazolino/iminopyrimidino/thioxopyrimidino imidazolines . Synthesis 2001 , 1509 – 1512 .
   Web of Science ®Google Scholar
• Cativiela , C. ; Diaz de Villegas , M. D. ; Melendez , E. Synthesis of methyl (Z/E)-2-acetamido(or benzamido)-3-aryl-2-butenoates . Tetrahedron 1986 , 42 , 583 – 590 .
   Web of Science ®Google Scholar
• (a) Yadav , L. D. S. ; Singh , A. Microwave activated solvent-free cascade reactions yielding highly functionalized 1,3-thiazines . Tetrahedron Lett. 2003 , 44 , 5637 – 5640 ; (b) Ghosh , S. ; Datta , D. B. ; Sen , N. Synthesis of N-(E)-(4-methoxystyryl)benzamide (alatamide) . Synthetic Commun. 1987 , 17 , 299 – 307 ; (c) Bautista , F. M. ; Campelo , J. M. ; Garcia , A. ; Luna , D. ; Marinas , J. M. ; Romero , A. A. Study on dry-media microwave azalactone synthesis on different supported KF catalysts: Influence of textural and acid-base properties of supports . J. Chem. Soc. Perkin Trans. 2 , 2002 , 227 – 234 .
   Web of Science ®Google Scholar
• Ghosh , S. ; Datta , D. B. ; Sen , N. Synthesis of N-(E)-(4-methoxystyryl)benzamide (alatamide) . Synthetic Commun. 1987 , 17 , 299 – 307 .
   Web of Science ®Google Scholar
• O'Reilly , N. J. ; Derwin , W. S. ; Lin , H. C. Optically pure (S)-6,7-dimethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid and asymmetric hydrogenation studies related to its preparation . Synthesis 1990 , 550 – 556 .
   Web of Science ®Google Scholar
• Berger , A. ; de Cian , A. ; Djukic , J.-P. ; Fischer , J. ; Pfeffer , M. Syntheses of ortho-mercurated and -palladated (η6-arene)tricarbonylchromium complexes . Organometallics 2001 , 20 , 3230 – 3240 .
   Web of Science ®Google Scholar
• Su , G. F. ; Wang , Z. C. ; Huang , W. Y. ; Wang , Z. X. ; Chen , Z. L. (Z)-Isobutyl 2-benzamido-3-(4-chlorophenyl)acrylate . Acta Cryst. E 2009 , 65 , o2890 .
   Google Scholar
• Palmer , R. A. ; Richards , A. J. ; Lisgarten , J. N. 2-Benzamido-3-(p-chlorophenyl)propenoic acid (antrex). Acta Cryst. C 1995 , 51 , 2338 – 2340 .
   Web of Science ®Google Scholar
• Huheey , J. E. ; Keiter , E. A. ; Keiter , R. L. Inorganic Chemistry: Principles of Structure and Reactivity, , 4th ed. ; Harper Collins : New York , 1993 ; p. 292 .
   Google Scholar
• Oxford Diffraction. CrysAlis RED. version 1.171.27p8. 2005, release CrysAlis171. NET, Abingdon, Oxford, England.
   Google Scholar
• Sheldrick , G. M. SADABS, 2008, University of Göttingen, Germany.
   Google Scholar
• Sheldrick , G. M. SHELXS-86 . Acta Crystallogr. 1990 , A46 , 467 .
   Web of Science ®Google Scholar
• Sheldrick , G. M. SHELXL-97: FORTRAN program for the refinement of crystal structures from diffraction data. Göttingen University, 1997. Molecular graphics were S23 done using the commercial package SHELXTL-PLUS, Release 5.05/V: © 1996, Siemens Analytical X-ray Instruments, Inc., Madison, Wisconsin.
   Google Scholar