Synthesis of (1,2,4-oxadiazole)palladium(II) complexes by [2 + 3] cycloaddition of nitrile oxides to organonitriles in the presence of PdCl 2

European Journal of Inorganic Chemistry

Volumn , Issue 5, 2005, Pages 845-853

  Bokach, Nadezhda A ^a,b   Kukushkin, Vadim Yu ^b   Haukka, Matti ^c   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^c UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

1,2,4 oxadiazole complexes; Cycloaddition; Nitrile complexes; Nitrile oxide complexes; Palladium

Indexed keywords

CHLORINE COMPOUNDS; CYANIDES; MASS SPECTROMETRY; NITROGEN OXIDES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

1,2,4-OXADIAZOLE COMPLEX; CONDITION; CYCLOADDITIONS; H NMR SPECTROSCOPY; NITRILE COMPLEXES; NITRILE OXIDE COMPLEX; NITRILE OXIDES; ORGANONITRILES; OXADIAZOLES; OXIDE COMPLEXES;

PALLADIUM COMPOUNDS;

(1,2,4 OXADIAZOLE)PALLADIUM; 1,2 BIS(DIPHENYLPHOSPHANYL)ETHANE; HETEROCYCLIC COMPOUND; LIGAND; NITRILE; NITRILE OXIDE; PALLADIUM CHLORIDE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLOADDITION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 16444365776     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400580     Document Type: Article

References (114)

1. a) J. C. Jochims, in Comprehensive Heterocyclic Chemistry II (Ed.: R. C. Storr), Elsevier, Oxford, UK 1996, 4, pp. 179 and 906; Chem. Abstr. 1997, 126, 157409;
2. a) J. C. Jochims, in Comprehensive Heterocyclic Chemistry II (Ed.: R. C. Storr), Elsevier, Oxford, UK 1996, 4, pp. 179 and 906; Chem. Abstr. 1997, 126, 157409;
3. b) K. Hemming, J. Chem. Res. S 2001, 209;
4. c) K. Hemming, J. Chem. Res. S 2001, 601:
5. d) A. G. Tyrkov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2000, 43, 73-77; Chem. Abstr. 2001, 134, 353264;
6. d) A. G. Tyrkov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2000, 43, 73-77; Chem. Abstr. 2001, 134, 353264;
7. e) I. Shibuya, Busshitsu Kogaku Kogyo Gijutsu Kenkyusho Hokoku 1999, 7, 283; Chem. Abstr. 2000, 133, 30676;
8. e) I. Shibuya, Busshitsu Kogaku Kogyo Gijutsu Kenkyusho Hokoku 1999, 7, 283; Chem. Abstr. 2000, 133, 30676;
9. f) L. B. Clapp, Adv. Heterocycl. Chem. 1976, 20, 65-116;
10. g) F. Eloy, R. Lenaers, Chim. Ther. 1966, 347-350; Chem. Abstr. 1967, 66, 37 793.
11. g) F. Eloy, R. Lenaers, Chim. Ther. 1966, 347-350; Chem. Abstr. 1967, 66, 37 793.
12. a) Z.-I. Terashita, K.-I. Naruo, S. Morimoto, PCT Int. Appl. WO 0260439, 2002; Chem. Abstr. 2002, 137, 145599;
13. b) Yu. S. Andreichikov, S. G. Pitirimova, I. V. Krylova, V. E. Kolla, E. V. Popov, USSR Pat. SU 1332767, 1990; Chem. Abstr. 1990, 113, 165416.
14. a) D. N. Nicolaides, K. C. Fylaktakidou, K. E. Litinas, D. Hadjipavlou-Litina, Eur. J. Med. Chem. 1998, 33, 715-724;
15. b) C. H. Mitch, H. E. Shannon, PCT Int. Appl. WO 9720561, 1997; Chem. Abstr. 1997, 127, 104351;
16. c) M. Yamamoto, Y. Ori, Jpn. Kokai Tokkyo Koho JP 6296480 [8796480], 1987; Chem. Abstr. 1987, 107, 115596:
17. d) Sumitomo Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho JP 6051188 [8551188], 1985; Chem. Abstr. 1985, 103, 71323;
18. e) Sumitomo Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho JP 8165881, 1981; Chem. Abstr. 1981, 95, 150674:
19. f) N. V. Gist-Brocades, Neth. Appl. NL 7807076, 1978; Chem. Abstr. 1978, 90, 121611;
20. g) F. M. Pallos, J. R. DeBaun, A. D. Gutman, US Pat., 3968224, 1976; Chem. Abstr. 1976, 85, 104204;
21. h) H. Breuer, U. D. Treuner, US Pat., 3887573, 1915; Chem. Abstr. 1975, 83, 97312;
22. i) U. D. Treuner, Ger. Offen., DE 2248940, 1973; Chem. Abstr. 1973, 79, 18719.
23. J. R. Romero, Expert Opin. Inv. Drug 2001, 10, 369; Chem. Abstr. 2001, 134, 246803.
24. J. R. Romero, Expert Opin. Inv. Drug 2001, 10, 369; Chem. Abstr. 2001, 134, 246803.
25. a) J. E. Macor, T. Ordway, R. L. Smith, P. R. Verhoest, R. A. Mack, J. Org. Chem. 1996, 61, 3228-3229:
26. b) D. A. Quagliato, P. M. Andrae, PCT Int. Appl. WO 0206250, 2002; Chem. Abstr. 2002, 136, 118440;
27. c) E. Gur, E. Dremencov, B. Lerer, M. E. Newman, Eur. J. Pharmacol. 2001, 411, 115-122;
28. d) J. Watson, J. V. Selkirk, A. M. Brown, J. Biomol. Screen. 1998, 3, 101-105:
29. e) P. J. Pauwels, T. Wurch, C. Palmier, F. C. Colpaert, Br. J. Pharmacol. 1998, 123, 51-62.
30. a) T. Naka, K. Kubo, Curr. Pharm. Design 1999, 5, 453-472;
31. b) H. Juraszyk, J. Gante, H. Wurziger, S. Bernotat-Danielowski, G. Melzer, PCT Int. Appl., 9744333, 1997; Chem. Abstr. 1997, 128, 23138.
32. a) H. Hagen, F. Becke, Ger. Offen., DE 2060082, 1972; Chem. Abstr. 1972, 77, 88511;
33. b) H. Hagen, F. Becke, J. Niemeyer, Ger. Offen., DE 2016692, 1971; Chem. Abstr. 1972, 76, 25299.
34. S. I. Torgova, L. A. Karamysheva, T. A. Geivandova, A. Strigazzi, Mol. Cryst. Liq. Cryst. A 2001, 365, 99-106.
35. a) A. Zamponi, M. Patsch, H. Hagen, B.-P. Walther, Ger. Offen., DE 19 640 189, 1998; Chem. Abstr. 1998, 128, 271684;
36. b) G. Lamm, H. Reichelt, M. Wiesenfeldt, Ger. Offen., DE 19 548 785, 1997; Chem. Abstr. 1997, 127, 110290;
37. c) H. Fuerstenwerth, Ger. Offen., DE 3 344 294. 1985; Chem. Abstr. 1985, 103:215 152.
38. a) G. Prossel, R. Erckel, E. Schinzel, D. Guenther, G. Roesch, Ger. Offen., DE 2748660, 1978; Chem. Abstr. 1978, 89, 112427;
39. b) H. Schlaepfer, Ger. Offen., DE 2712409, 1977; Chem. Abstr. 1978, 88, 51973;
40. c) A. E. Siegrist, G. Kormany, G. Kabas, Helv. Chim. Acta 1976, 59, 2469-2491;
41. d) A. Domerque, Ger. Offen., DE 2503439, 1975; Chem. Abstr. 1975, 83, 165830.
42. a) A. S. Da Silva, M. A. A. De Silva, C. E. M. Carvalho, O. A. C. Antunes, J. O. M. Herrera, I. M. Brinn, A. S. Mangrich, Inorg. Chim. Acta 1999, 292, 1-6;
43. b) G. Orellana, C. Alvarez-Ibarra, M. Luz.Quiroga, Bull. Soc. Chim. Belg. 1988, 97, 731-741;
44. c) Yu. I. Ryabukhin, N. V. Shibaeva, A. S. Kuzharov, V. G. Korobkova, A. V. Khokhlov, A. D. Garnovskii, Koord. Khim. 1987, 13, 869-874;
45. d) H. A. Goodwin, F. E. Smith, Inorg. Nucl. Chem. Lett. 1974, 10, 99-103.
46. For recent references see: a) M. Du, Y.-M. Guo, S.-T. Chen, X.-H. Bu, S. R. Batten, J. Ribas, S. Kitagawa, Inorg. Chem. 2004, 43, 1287-93:
47. b) D. Huang, H.-B. Song, M. Du, S.-T. Chen, X.-H. Bu, J. Ribas, Inorg. Chem. 2004, 43, 931-944;
48. c) H. Hou, L. Xie, G. Li, T. Ge, Y. Fan, Y. Zhu, New J. Chem. 2004, 28, 191-199;
49. d) Y.-B. Dong, J.-P. Ma, R.-Q. Huang, F.-Z. Liang, M. D. Smith, Dalton Trans. 2003, 1472-1479;
50. e) Y.-B. Dong, J.-Y. Cheng, R.-Q. Huang, M. D. Smith, H.-C. Zur Loye, Inorg. Chem. 2003, 42, 5699-5706;
51. f) M. Du, X.-H. Bu, Z. Huang, S.-T. Chen, Y.-M. Guo, C. Diaz, J. Ribas, Inorg. Chem. 2003, 42, 552-559;
52. g) Y.-B. Dong, X.-B. Ma, R.-Q. Huang, M. D. Smith, H.-C. Zur Loye, Inorg. Chem. 2003, 42, 294-300;
53. h) M. Du, X.-H. Bu, Y.-M. Guo, H. Liu, S. R. Batten, J. Ribas, T. C. W. Mak, Inorg. Chem. 2002, 41, 4904-4908.
54. C. Incarvito, A. L. Rheingold, C. J. Qin, A. L. Gavrilova, B. Bosnich, Inorg. Chem. 2001, 40, 1386-1390.
55. A. Vlcek, Jr., Chemtracts 2002, 15, 49.
56. a) N.-X. Hu, M. Esteghamatian, S. Xie, Z. Popovich, A.-M. Hor, B. Ong, S. Wang, Adv. Mater. 1999, 11, 1460-1463;
57. b) J. F. Wang, G. E. Jabbour, E. A. Mash, J. Anderson, Y. Zhang, P. A. Lee, N. R. Armstrong, N. Peyghambarian, B. Kippelen, Adv. Mater. 1999, 11, 1266-1269.
58. a) P. Gomez-Saiz, J. Garcia-Tojal, M. A. Maestro, J. Mahia, F. J. Arnaiz, L. Lezama, T. Rojo, Eur. J. Inorg. Chem. 2003, 2639-2650;
59. b) P. Gomez-Saiz, J. Garcia-Tojal, F. J. Arnaiz, M. A. Maestro, L. Lezama, T. Rojo, Inorg. Chem. Commun. 2003, 6, 558-560;
60. c) P. Gomez-Saiz, J. Garcia-Tojal, M. A. Maestro, F. J. Arnaiz, T. Rojo, Inorg. Chem. 2002, 41, 1345-1347.
61. C. K. Lai, C.-R. Wen, J.-H. Sung, 224th ACS National Meeting, Boston, MA, United States, August 18-22, 2002, INOR-413, Am. Chem. Soc.: Washington, D.C.
62. a) G. Wagner, A. J. L. Pombeiro, V. Yu. Kukushkin, J. Am. Chem. Soc. 2000, 122, 3106-3111;
63. b) G. Wagner, M. Haukka, J. J. R. Frausto da Silva, A. J. L. Pombeiro, V. Yu. Kukushkin, Inorg. Chem. 2001, 40, 264-271;
64. c) M. A. J. Charmier, V. Yu. Kukushkin, A. J. L. Pombeiro, Dalton Trans. 2003, 2540-2543;
65. d) M. L. Kuznetsov, V. Yu. Kukushkin, M. Haukka, A. J. L. Pombeiro, Inorg. Chim. Acta 2003, 356, 85-94 (special volume dedicated to J. J. R. Fraústo da Silva).
66. N. A. Bokach, A. V. Khripoun, V. Yu. Kukushkin, M. Haukka, A. J. L. Pombeiro, Inorg. Chem. 2003, 42, 896-903.
67. V. Yu. Kukushkin, A. J. L. Pombeiro, Chem. Rev. 2002, 102, 1771-1802 and references cited therein.
68. A. J. L. Pombeiro, V. Yu. Kukushkin, in Comprehensive Coordination Chemistry, 2nd Edition, Elsevier, 2003, vol. 1, pp. 639-660.
69. M. L. Kuznetsov, V. Yu. Kukushkin, A. I. Dementev, A. J. L. Pombeiro, J. Phys. Chem. A 2003, 107, 6108-6120.
70. Ch. Grundmann, J. M. Dean, J. Org. Chem. 1965, 30, 2809-2812.
71. a) G. K. Anderson, M. Lin, Inorg. Synth. 1990, 28, 60-63;
72. b) F. L. Wimmer, S. Wimmer, P. Castan, R. J. Puddephatt, Inorg. Synth. 1992, 29, 185-187;
73. c) I. E. Bekk, E. V. Gusevskaya, V. A. Likholobov, Yu. I. Ermakov, React. Kinet. Catal. Lett. 1987, 33, 209-214:
74. d) M. A. Andrews, T. C. T. Chang, C. W. F. Cheng, T. J. Emge, K. P. Kelly, T. F. Koetzle, J. Am. Chem. Soc. 1984, 106, 5913-5920;
75. e) B. B. Wayland, R. F. Schramm, Inorg. Chem. 1969, 8, 971-976;
76. f) M. E. S. Doria, E. M. P. R. Branco, M. F. C. Guedes da Silva, A. J. L. Pombeiro, R. A. Michelin, R. Bertani, M. Mozzon, Portugal. Electrochim. Acta 1995, 13, 325-328.
77. S. Kanemasa, S. Kobayashi, Bull. Chem. Soc. Jpn. 1993, 66, 2685-2693.
78. S. Kanemasa, S. Kobayashi, M. Nishiuchi, H. Yamamoto, E. Wada, Tetrahedron Lett. 1991, 32, 6367-6370.
79. S. Kanemasa, M. Nishiuchi, E. Wada, Tetrahedron Lett. 1992, 33, 1357-1360.
80. H. R. Kim, J. H. Song, S. Y. Rhie, E. K. Ryu, Synth. Commun. 1995, 25, 1801-1807.
81. A. Kamimura, Y. Kaneko, A. Ohta, K. Matsuura, Y. Fujimoto, A. Kakehi, S. Kanemasa, Tetrahedron 2002, 58, 9613-9620.
82. P. Perez, L. R. Domingo, M. J. Aurel, R. Contreras, Tetrahedron 2003, 59, 3117-3125.
83. a) L. Prasad, Y. Le Page, F. E. Smith, Acta Crystallogr., Sect. B 1982, 38, 2890-2893;
84. b) B. J. Childs, D. C. Craig, M. L. Scudder, H. A. Goodwin, Aust. J. Chem. 1999, 52, 673-680.
85. a) L. Golic, I. Leban, B. Stanovnik, M. Tisler, Acta Crystallogr., Sect B 1979, 35, 2256-2258;
86. b) A. Albinati, S. Bruckner, Acta Crystallogr., Sect B 1978, 34, 3390-3392;
87. c) J. B. Press, N. H. Eudy, F. M. Lovell, G. O. Morton, M. M. Siegel, J. Am. Chem. Soc. 1982, 104, 4013-4014.
88. a) K. Horvath, D. Korbonits, G. Naray-Szabo, K. Simon, J. Mol. Struct. 1986, 136, 215-227;
89. b) L. Eberson, J. L. Calvert, M. P. Harishom, W. T. Robinson, Acta Chem. Scand. 1994, 48, 347-355;
90. c) R. Baker, G. A. Showell, L. J. Street, J. Saunders, K. Hoogsteen, S. B. Freedman, R. Hargreaves, J. Chem. Soc., Chem. Commun. 1992, 817-819.
91. a) H. Batista, G. B. Carpenter, R. M. Srivastava, J. Chem. Cryst. 2000, 30, 131-134;
92. b) S. A. Hewlins, J. A. Murphy, J. Lin, D. E. Hibbs, M. B. Hursthouse, J. Chem. Soc., Perkin Trans. 1 1997, 1559-1570.
93. a) I. P. Smoliakova, K. J. Keuseman, D. C. Haagenson, D. M. Wellmann, P. B. Colligan, N. A. Kataeva, A. V. Churakov, L. G. Kuz'mina, V. V. Dunina, J. Organomet. Chem. 2000, 603, 86-97;
94. b) M. Mitewa, T. Todorov, G. Gencheva, O. Angelova, T. N. Bakalova J. Coord. Chem. 2002, 55, 1367-1372;
95. c) K. Kurdziel, T. Glowiak, J. Coord Chem. 2002, 55, 327-334;
96. d) N. Bharti, Shailendra; S. J. Coles, M. B. Hursthouse, T. A. Mayer, M. T. G. Garza, D. E. Cruz-Vega, B. D. Mata-Cardenas, F. Naqvi, M. R. Maurya, A. Azam, Helv. Chim. Acta 2002, 85, 2704-2712;
97. e) H. Oshio, A. Oh'to, T. Ito, Chem. Commun. 1996, 1541-1542.
98. f) S. Zen, T. Nishino, K. Harada, H. Nakamura, Y. Iitaka, Chem. Pharm. Bull. 1983, 31, 4181-4184.
99. g) P. S. Jarrett, O. M. Ni Dhubhghaill, P. J. Sadler, J. Chem. Soc., Dalton Trans. 1993, 1863-1870.
100. a) F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2003, 125, 9983-9987;
101. b) F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12 210-12 216;
102. c) Z. P. Demko, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2113-2116;
103. d) Z. P. Demko, K. B. Sharpless, Org. Lett. 2001, 3, 4091-4094;
104. e) Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66, 7945-7950;
105. f) K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449-1458;
106. g) K. V. Gothelf, K. B. Jensen, K. A. Jørgensen, Sci. Prog. 1999, 82, 327-350;
107. h) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-909;
108. i) S. Kobayashi, K. A. Jørgensen, Cycloaddition Reactions in Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2002.
109. Z. Otwinowski, W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode, in Methods in Enzymology, vol. 276, Macromolecular Crystallography, part A (Eds.: C. W. Carter, Jr., R. M. Sweet), Academic Press, New York, 1997, pp. 307-326.
110. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
111. G. M. Sheldrick, SHELXS-97; University of Göttingen, Germany, 1997.
112. P. T. Beurskens, G. Beurskens, R. de Gelder, S. Garcia-Granda, R. O. Gould, R. Israel, J. M. M. Smits, The DIRDIF-99 program system, Crystallography Laboratory, University of Nijmegen, The Netherlands, 1999.
113. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.
114. G. M. Sheldrick, SHELXTL v. 6.12, Bruker Analytical X-ray Systems, Bruker AXS, Inc. Madison, Wisconsin, USA, 2002.