Synthesis and characterization of two dehydroacetic acid derivatives and molybdenum(V) complexes: an NMR and crystallographic study

Two enaminones ethyl 4-(4-hydroxy-6-methyl-2H-pyran-2-on-3-yl)-2-(tryptamino)-4-oxo-2-butenoate (HL 1 ) and 3-(1-tryptaminoetylidene)-6-methyl-2H-pyran-2,4(3H)-dione (HL 2 ) have been prepared by the reactions of tryptamine with 2-hydroxy-4-(4-hydroxy)-6methyl)-2Hbb-pyrane-2-on-3-yl)-4-oxo-2-butenoate (ehmpb) or with dehydroacetic acid (dha). The NMR spectroscopy confirmed that both tautomeric forms of HL 1 : endo-enol (tautomer A with hydroxyl group at position 4) and exo-enol form (tautomer B with hydroxyl group at position 7) are present in the DMSO-d6 solution. The molecular and crystal structure as well as the NMR data of HL 2 showed that

[1]  M. Cindrić,et al.  The new molybdenum(V) complexes with differently N-substituted β′-hydroxy-β-enaminones , 2004 .

[2]  Seth M. Cohen,et al.  Examination of novel zinc-binding groups for use in matrix metalloproteinase inhibitors. , 2003, Inorganic chemistry.

[3]  S. Fujii,et al.  A New Method for Synthesis of Crown Ether Type Pyridinophanes , 2003 .

[4]  K. Saatchi,et al.  Synthesis and solution studies of the complexes of pyrone analogue ligands with vanadium(IV) and vanadium(V) , 2002 .

[5]  G. Giester,et al.  New Dinuclear Molybdenum(V) Complexes With β′-Hydroxy-β-enaminones Containing a 4-Hydroxy-2-pyrone Ring , 2002 .

[6]  M. Cindrić,et al.  Synthesis and characterization of new dinuclear complexes of molybdenum(V) with β′-hydroxy-β-enaminones , 2002 .

[7]  J. D. Figueroa-Villar,et al.  Synthesis and structure of cadmium and zinc complexes of dehydroacetic acid , 2002 .

[8]  M. Cindrić,et al.  Synthesis and Structure of Two Isomeric Enaminones , 2001 .

[9]  Valerio Bertolasi,et al.  Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation , 2000 .

[10]  I. Fábián,et al.  Speciation and NMR relaxation studies of VO(IV) complexes with several O-donor containing ligands: oxalate, malonate, maltolate and kojate , 2000 .

[11]  M. Cindrić,et al.  Hexanuclear complexes of molybdenum(V) containing [Mo6O12(OCH3)4(acac)3]− anion , 2000 .

[12]  E. Monzani,et al.  Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid , 2000, JBIC Journal of Biological Inorganic Chemistry.

[13]  M. Cindrić,et al.  Synthesis and Structures of New Enaminones , 2000 .

[14]  M. Yamaguchi,et al.  Convenient Synthesis of Chiral Cyclophanes that Can Coordinate to Metals , 1999 .

[15]  E. Essassi,et al.  Reaction of Aminobenzimidazoles with 4-Hydroxy-6-methyl-2-pyrone and 4-Hydroxycoumarine , 1999 .

[16]  N. Taylor,et al.  Synthesis, characterization, and biological relevance of hydroxypyrone and hydroxypyridinone complexes of molybdenum , 1999 .

[17]  P. Iyer,et al.  Chiral Mn(III) Schiff base complex catalyzed aerobic enantioselective epoxidation of prochiral non-functionalized olefins , 1999 .

[18]  S. Maitra,et al.  Reaction of Dehydroacetic Acid with Aliphatic, Aromatic and Heterocyclic Amines. , 1998 .

[19]  P. Iyer,et al.  Chiral Ru(III) metal complex-catalyzed aerobic enantioselective epoxidation of styrene derivatives with co-oxidation of aldehyde , 1997 .

[20]  B C Finzel,et al.  Structure-based design of HIV protease inhibitors: 5,6-dihydro-4-hydroxy-2-pyrones as effective, nonpeptidic inhibitors. , 1996, Journal of medicinal chemistry.

[21]  J. Elguero,et al.  THE STRUCTURE OF THE COMPOUNDS RESULTING FROM THE REACTION OF ARYLHYDRAZINES WITH DEHYDROACETIC ACID : AN NMR AND CRYSTALLOGRAPHIC STUDY , 1995 .

[22]  L. Somogyi.  Cyclization reactions of tricarbonylmethane thiosemicarbazones: Formation of 1,3,4-thiadiazole derivatives with concomitant CC bond cleavage , 1995 .

[23]  Zijian Guo,et al.  Palladium(II) and platinum(II) complexes with N-substituted methionines , 1995 .

[24]  N. R. Rao,et al.  Facile Synthesis of Some New Macrocyclic Imine Ligands from Dehydroacetic Acid. , 1994 .

[25]  D. van der Helm,et al.  3-[1-(Ethylamino)ethylidene]-6-methyl-3H-pyran-2,4-dione. , 1993, Acta crystallographica. Section C, Crystal structure communications.

[26]  Shuang Liu,et al.  Synthesis and characterization of a pentadentate Schiff base N3O2 ligand and its neutral technetium(V) complex. X-ray structure of {N,N'-3-azapentane-1,5-diylbis(3-(1-iminoethyl)-6-methyl-2H-pyran-2,4(3H)-dionato)(3-)-O,O',N,N',N''}oxotechnetium(V) , 1991 .

[27]  O. Carugo,et al.  Influence of the complexation of copper(II) on the structure and reactivity of 4-hydroxy-6-methyl-3-[3-dimethylaminoacryloyl]-2H-pyran-2-one , 1990 .

[28]  V. Bertolasi,et al.  Evidence for resonance-assisted hydrogen bonding from crystal-structure correlations on the enol form of the .beta.-diketone fragment , 1989 .

[29]  B. Katušin-Ražem,et al.  Reactions of ethyl 2-hydroxy-4-(4-hydroxy-6-methyl-2-pyron-3-yl)-4-oxo-2-butenoate with N-nucleophiles. Synthesis of isomeric pyronylpyrazoles and pyrano[4,3-c]pyrazoles , 1989 .

[30]  G. Parker.  Analytical Chemistry of Molybdenum , 1983 .

[31]  K. Ang,et al.  1 H, 13C, and 15N nuclear magnetic resonance studies on the tautomerism of the Schiff's bases of 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione and 3,5-diacetyltetrahydropyran-2,4,6-trione , 1982 .

[32]  G. Zanotti,et al.  The crystal and molecular structure of 3-[1-(phenylamino)ethylidene]-6-methyl-2,4-dioxo-2,3-dihydro-4H-pyran , 1978 .

[33]  R. E. Rice,et al.  Physicochemical and spectral properties of octahedral dioxomolybdenum(VI) complexes , 1968 .