1,2-Diaryl(3-pyridyl)ethanone oximes. Intermolecular hydrogen bonding networks revealed by X-ray diffraction

Molecules

Volumn 13, Issue 2, 2008, Pages 301-318

  Alcalde, Ermitas ^a   Mesquida, Neus ^a   Alvarez Rúa, Carmen ^b   Cuberes, Rosa ^c   Frigola, Jordi ^c   García Granda, Santiago ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF OVIEDO   (Spain)

^c Laboratorios Dr Esteve SA   (Spain)

Author keywords

Ethanones; Hydrogen bonds; Oximes; Self assembly; X ray diffraction crystallography

Indexed keywords

OXIME; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXIMES; PROTONS; X-RAY DIFFRACTION;

EID: 40349096452     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13020301     Document Type: Article

References (44)

1. (a) Veeramaneni, V. R.; Pal, M.; Yeleswarapu, K. R. A high speed parallel synthesis of 1,2-diaryl-1-ethanones via a clean-chemistry C-C bond formation reaction. Tetrahedron 2003, 59, 3283-3290;
2. (b) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Akhmedova, R. G. A convenient access to 1-substituted-2-azinyl-1-ethanones via acylation of alkylated azines with N-acylbenzotriazoles. Arkivoc 2005, 329-338.
3. Merkul, E.; Müller, J. J. A new consecutive three-component oxazole synthesis by an amidation-coupling-cycloisomerization (ACCI) sequence. Chem. Commun. 2006, 4817-4819.
4. Davies, I. W.; Marcoux, J. F.; Corley, E. G.; Journet, M.; Cai, D. -W.; Palucki, M.; Wu, J.; Larsen, R. D.; Rossen, K.; Pye, P. J.; DiMichele, L.; Dormer P.; Reider, P. J. A Practical Synthesis of a COX-2-Specific Inhibitor. J. Org. Chem., 2000, 65, 8415-8420.
5. (a) Hashimoto, H.; Imamura, K.; Haruta J.; Wakitani, K. 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as Selective Cyclooxigenase-2 Inhibitors: Enhancement of the Selectivity by Introduction of a Fluorine Atom and Identification of a Potent, Highly Selective, and Orally Active COX-2 Inhibitor JTE-522. J. Med. Chem. 2002, 45, 1511-1517;
6. (b) Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel B. S.; Seibert, K. 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, Valdecoxib: A Potent and Selective Inhibitor of COX-2. J. Med. Chem. 2000, 43, 775-777.
7. Marcoux, J. F.; Corley, E. G.; Rossen, K.; Pye, P. J. M.; Wu, J.; Robbins, M. A.; Davies, I. W.; Larsen, R. D.; Reider, P. J. Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines. Org. Lett. 2000, 2, 2339-2341 and references cited therein.
8. Etter, M. C. Encoding and Decoding Hydrogen-Bond Patterns of Organic Compounds. Acc. Chem. Res. 1990, 23, 120-126.
9. (a) Steiner, T. The hydrogen bond in the solid state. Angew. Chem. Int. Ed. 2002, 41, 4-76;
10. (b) Steiner, T. C-H⋯O hydrogen bonding in crystals. Crystallogr. Rev. 2003, 9, 177-228.
11. (a) Aakeröy, C. B.; Beatty A. M.; Leinen, D. S. The Oxime Functionality: A Versatile Tool for Supramolecular Assembly of Metal-Containing Hydrogen-Bonded Architectures. J. Am. Chem. Soc. 1998, 120, 7383-7384 and references cited therein;
12. (b) Aakeröy, C. B.; Beatty A. M.; Leinen, D. S. New building blocks for crystal engineering. Syntheses and crystal structures of oxime-substituted pyridines. CrystEngComm. 2000, 2, 1-6 and references cited therein;
13. (c) Bruton, E. A.; Brammer, L.; Pigge, F. C.; Aakeröy, C. B.; Leinen, D. S. Hydrogen bond patterns in aromatic and aliphatic dioximes. New J. Chem. 2003, 27, 1084-1094;
14. (d) Aakeröy, C. B.; Desper, J.; Scott, B. M. T. Balancing supramolecular reagents for reliable formation of co-crystals. ChemCommun. 2006, 1445-1447;
15. (e) Aakeröy, C. B.; Salmon, D. J.; Smith, M. M.; Desper, J. Cyanopheniloximes: Reliable and Versatile Tools for Hydrogen-Bond Directed Supramolecular Synthesis of Cocrystals. Crystal Growth & Desig 2006, 6, 1033-1042 and references cited therein;
16. (f) Aakeröy C. B.; Schultheiss, N.; Desper, J. A pyridyl-functionalized cavitand. Starting point for hydrogen-bond driven assembly for heterodimeric capsules. CrystEngComm. 2006, 8, 502-506.
17. (a) Mazik, M.; Bläser, D.; Boese, R. Programmed Construction of Discrete Self-Assembled Cyclic Aggregates. Chem. Eur. J. 2000, 6, 2865-2873;
18. (b) Mazik, M.; Bläser, D.; Boese, R. α,β-Unsaturated Ketoximes Carrying a Terminal Pyridine or Quinoline Subunit as Building Blocks for Supramolecular Syntheses. J. Org. Chem. 2005, 70, 9115-9122;
19. (c) Marsman, A. W.; van Walree, C. A.; Havenith, R. W. A.; Jenneskens, L. W.; Lutz, M.; Spek, A. L.; Egbertus, T. G.; Lutz, E. T. G.; van der Maas, J. H. Infinite, undulating chains of intermolecularly hydrogen bonded (E,E)-2,2-dimethylcyclohexane-1,3-dione dioximes in the solid state. A single crystal Xray, charge density distribution and spectroscopic study. J. Chem. Soc., Perkin Trans. 2000, 501-510.
20. (a) Chertanova, L.; Pascard, C. X-ray Investigation of Glyoxime Derivatives. V. Two Isomers of 2-(Thienyl)glyoxime. A Database Study of the Geometry and Hydrogen Bonding of the Oxime Group. Acta Crys. 1994, B50, 708-716;
21. (b) Maurin, J. K. Oxime-Carboxyl Hydrogen Bonds: the Preferred Interaction Determining Crystal Packing of 'Carboxyoximes'. Acta Crys. 1998, B54, 866-871;
22. (c) Hoogesteger, F. J.; Jenneskensa, L. W.; Veldmanh, H. K. N.; Spekh, A. L. Self-Complementary Hydrogen Bonding of 1,1′-Bicyclohexylidene-4, 4′-dione Dioxime. Formation of a Non-Covalent Polymer. Tetrahedron 1996, 52, 1773-1784.
23. (a) Nishio, M. CH/π hydrogen bonds in crystals. CrystEngComm. 2004, 6, 130-158;
24. (b) Nishio, M. CH/π hydrogen bonds in organic reactions. Tetrahedron 2005, 61, 6923-6950.
25. 2-CO-Ar′] [1,4] required for synthesis of selective COX-2 inhibitors, see: (a) Singh, S. K.; Saibaba, V.; Ravikumar, V.; Rudrawar, S. V.; Daga, P.; Rao, C. S.; Akhila, V.; Hegde P.; Rao, Y. K. Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors. Bioorg. Med. Chem. 2004, 12, 1881-1893;
26. (b) Baruah, B.; Dasu, K.; Vaitilingam, B.; Vanguri, A.; Casturi, S. R.; Yeleswarapu, K. R. 1,2-Diaryl-1-ethanone and pyrazolo [4,3-c] quinoline-4-one as novel selective cyclooxigenase-2-inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 445-448.
27. 2-(3-Py)], see: (a) Chen, H. Y.; Kim, S.; Wu, J. Y.; Birzin, E. T.; Chan, W.; Yang, Y. T.; Dahllund, J.; DiNinno, F.; Rohrer, S. P.; Schaeffer, J. M.; Hammond, M. L. Estrogen receptor ligands. Part 3: The SAR of dihydrobenzoxathiin SERMs. Bioorg. Med. Chem. Lett. 2004, 14, 2551-2554;
28. (b) Biftu, T.; Feng, D.; Ponpipom, M.; Girotra, N.; Liang, G. -L.; Qian, X.; Bugianesi, R.; Simeone, J.; Chang, L.; Gurnett, A.; Liberator, P.; Dulski, P.; Leavitt, P. S.; Crumley, T.; Misura, A.; Murphy, T.; Rattray, S.; Samaras, S.; Tamas, T.; Mathew, J.; Brown, C.; Thompson, D.; Schmatz, D.; Fisher M.; Wyvratt, M. Synthesis and SAR of 2,3-diarylpyrrole inhibitors of parasite cGMP-dependent protein kinase as novel anticoccidial agents. Bioorg. Med. Chem. Lett. 2005, 15, 3296-3301.
29. (a) Wehmeyer R. M.; Rieke, R. D. Direct formation of functionalized ketones via the coupling of functionalized organocopper reagents with acid chlorides. Tetrahedron Lett. 1988, 29, 4513-4516;
30. (b) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. The Direct Formation of Functionalized Alkyl(aryl)zinc Halides by Oxidative Addition of Highly Reactive Zinc with Organic Halides and Their Reactions with Acid Chlorides, α,β-Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides. J. Org. Chem. 1991, 56, 1445-1453;
31. (c) Rieke, R. D.; Hanson, M. V.; Brown, J. D. Direct Formation of Secondary and Tertiary Alkylzinc Bromides and Subsequent Cu(I)-Mediated Couplings. J. Org. Chem. 1996, 61, 2726-2730.
32. Singh, J.; Satyamurthi, N.; Aidhen, I. S. The Growing Synthetic Utility of Weinreb's Amide. J. Prakt. Chem. 2000, 342, 340-347.
33. (a) Maryanoff, B. E.; Reitz, A. B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev. 1989, 89, 863-97;
34. (b) Journet, M.; Cai, D.; Larsen, R. D.; Reider, P. J. An Improved and Practical Procedure for the Synthesis of Substituted Phenylacetylpyridines. Tetrahedron Lett. 1998, 39, 1717-1720 and references cited therein;
35. (c) Piva, O.; Comesse, S. Tandem Michael-Wittig-Horner Reaction: One-Pot Synthesis of δ-Substituted α,β-Unsaturated Carboxylic Acid Derivatives - Application to a Concise Synthesis of (Z)- and (E)-Ochtoden-1-al Eur. J. Org. Chem. 2000, 2417-2424.
36. Kolehmainen, E.; Gawinecki, R.; Osmialowski, B.; Trzebiatowska, K. NMR Spectral Assignment of Substituted Salicylaldoximes by Inverse Pulse Techniques with z-Gradient Selection: Correlation of NMR Parameters with Substituent Constants. Mag. Res. Chem. 1997, 35, 778-784 and references cited therein.
37. 1/c-, the asymmetric unit contained one independent oxime molecule.
38. Zhu, L.; Rieke, R. D. A facile method for the preparation of functionalized 2,3-disubstituted-1,3-butadienes. Tetrahedron Letters 1991, 32, 2865-2866.
39. Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Electrophilic amination of organozinc halides. Tetrahedron Letters 1998, 38, 9157-9160.
40. Bruker. COLLECT data collection software. Bruker AXS: Delft, The Netherlands, 2004.
41. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 1997, 276, 307-326.
42. Blessing, R. H. An Empirical Correction for Absorption Anisotropy. Acta Cryst. 1995, A51, 33-38.
43. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. Completion and Refinement of Crystal Structures with SIR92. J. Appl. Cryst. 1993, 26, 343-350.
44. Sheldrick, G. M. SHELXL-97. University of Göttingen: Germany, 1997.