Platinum(II)-Complexed tetrahydroimidazo[1,2-b][1,2,4]oxadiazoles derived from Metal-Mediated 1,3-Dipolar cycloaddition. Novel type of heterocycles, which do not exist without the metal center

Organometallics

Volumn 28, Issue 5, 2009, Pages 1406-1413

  Bokach, Nadezhda A ^a   Kuznetsov, Maxim L ^b   Haukka, Matti ^c   Ovcharenko, Victor I ^d   Tretyakov, Eugeny V ^d   Kukushkin, Vadim Yu ^a,e  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b MOSCOW STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^c UNIVERSITY OF EASTERN FINLAND   (Finland)

^d INTERNATIONAL TOMOGRAPHY CENTER   (Russian Federation)

^e INSTITUTE OF MACROMOLECULAR COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTIONS; DIPOLAR CYCLOADDITION; ELEMENTAL ANALYSIS; EXPERIMENTAL OBSERVATIONS; HETERO-CYCLES; HETEROCYCLIC LIGANDS; IMIDAZOLINE; KINETIC FACTORS; METAL CENTERS; NMR SPECTROSCOPIES; OXADIAZOLE; OXADIAZOLES; PROTONATED; TETRAMETHYL; X-RAY DATUM;

CYANIDES; CYCLOADDITION; ETHANE; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM;

LIGANDS;

EID: 64749099366     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800963d     Document Type: Article

References (88)

1. (a) Torssel, K. B. G. Nitrile oxides, nitrones and nitronates in organic synthesis, novel strategies in synthesis (organic nitro chemistry; 2); VCH Publishers, Inc, 1988.
2. (b) Osborn, H. M. I.; Gemmell, V.; Harwood, L. M. J. Chem. Soc., Perkin Trans. 1 2002, 2419.
3. (c) Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247.
4. (d) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
5. (e) Broggini. G.; Molteni, G.; Terraneo, A.; Zecchi, G. Heterocycles 2003, 59, 823.
6. (a) Bokach, N. A.; Kukushkin, V. Yu. Russ. Chem. Bull. 2006, 55, 1869.
7. (b) Plate, R.; Hermkens, P. H. H.: Smits, J. M. M.; Nivard, R. J. F.; Ottenheijm, H. C. J. J. Org. Chem. 1987, 52, 1047.
8. (c) Hermkens, P. H. H.; Maarseveen. J. H. v.; Kruse, C. G.; Scheeren, H. W. Tetrahedron 1988, 44, 6491.
9. (a) Kukushkin, V. Yu.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771.
10. (b) Pombeiro, A. J. L.; Kukushkin, V. Yu. Reactions of Coordinated Nitriles. In Comprehensive Coordination Chemistry, 2nd ed.; Elsevier, 2004; Chapter 1.34, Vol. 1, pp 639-660.
11. (c) Michelin, R. A.; Mozzon, M.; Bertani, R. Coord. Chem. Rev. 1996, 147, 299.
12. (d) Eglin, J. Comments Inorg. Chem. 2002, 23, 23.
13. (e) Murahashi. S. I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225.
14. (f) Kukushkin, Yu. N. Russ. J. Coord. Chem. 1998, 24, 173.
15. (g) Parkins, A. W. Platinum Metals Rev. 1996, 40, 169.
16. (h) da Rocha. Z. N.; Chiericato. G., Jr.; Tfouni, E. Adv. Chem. Ser. 1997, 297.
17. (i) Corain, B.; Basato, M.; Veronese, A. C. J. Mol. Catal. 1993, 81, 133.
18. (j) Chin. J. Acc. Chem. Res. 1991, 24, 145.
19. (a) Wagner, G.; Pombeiro, A. J. L.; Kukushkin, V. Yu. J. Am. Chem. Soc. 2000, 122, 3106.
20. (b) Wagner, G.; Haukka, M.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L.; Kukushkin, V. Yu. Inorg. Chem. 2001, 40, 264.
21. (c) Bokach, N. A.; Krokhin, A. V.; Nazarov, A. A.; Kukushkin, V. Yu.; Haukka, M.; Fraustoda Silva, J. J. R.; Pombeiro, A. J. L. Eur. J. Inorg. Chem. 2005, 3042.
22. (d) Charmier, M. A. J.; Kukushkin, V. Yu.; Pombeiro, A. J. L. Dalton Trans. 2003, 2540.
23. (e) Bokach. N. A.; Khripoun. A. V.; Kukushkin. V. Yu.; Haukka, M.; Pombeiro, A. J. L. Inorg. Chem. 2003, 42, 896.
24. (f) Bokach, N. A.; Kukushkin, V. Yu.; Haukka, M.; Pombeiro, A. J. L. Eur. J. Inorg. Chem. 2005, 845.
25. (g) Makarycheva-Mikhailova, A. V.; Golenetskaya, J. A.; Bokach. N. A.; Balova, I. A.; Haukka, M.; Kukushkin, V. Yu. Inorg. Chem. 2007, 46, 8323.
26. (h) Wagner. G.; Haukka, M. Dalton Trans. 2001, 2690.
27. (i) Desai. B.; Danks, T. N.: Wagner, G. Dalton Trans. 2003, 2544.
28. (a) Kuznetsov, M. L.; Kukushkin, V. Yu. J. Org. Chem. 2006, 71, 582.
29. (b) Kuznetsov. M. L.; Nazarov, A. A.; Kozlova, L. V.; Kukushkin, V. Yu. J. Org. Chem. 2007, 72, 4475.
30. (c) Kuznetsov, M. L.; Kukushkin, V. Yu.; Dement'ev, A. I.; Pombeiro, A. J. L. J. Phvs. Chem. A 2003, 107, 6108.
31. (d) Special volume dedicated to J. J. R. Frausto da Silva: Kuznetsov, M. L.; Kukushkin, V. Yu.; Haukka, M.; Pombeiro, A. J. L. Inorg. Chim. Acta 2003, 356, 85.
32. (a) Himo, F.; Demko, Z. P.; Noodleman. L.; Sharpless, K. B. J. Am. Chem. Soc. 2003, 125, 9983.
33. (b) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J. Am. Chem. Soc. 2002, 124, 12210.
34. (c) Demko, Z. P.; Sharpless. K. B. Org. Lett. 2001, 3, 4091.
35. (d) Demko, Z. P.; Sharpless. K. B. J. Org. Chem. 2001, 66, 7945.
36. (e) Wang, X. S.; Tang. Y. Z.; Huang, X. F.; Qu, Z. R.; Che, C. M.; Chan, P. W. H.; Xiong, R. G. Inorg. Chem. 2005, 44, 5278.
37. Jones, R. C. F.; Martin, J. N.; Smith, P.; Gelbrich, T.; Light, M. E.; Hursthouse, M. B. Chem. Commun. 2000, 1949.
38. (a) Popov, S. A.; Romanenko, G. V.; Reznikov, V. A.J. Mol. Struct. 2008, 872. 30.
39. (b) Popov. S. A.; Reznikov, V. A. J. Heterocycl. Chem. 2007, 43, 293.
40. (c) Popov. S. A.; Chukanov, N. V.; Romanenko, G. V.; Rybalova, T. V.; Gatilov. Y. V.; Reznikov. V. A. J. Hetercycl. Chem. 2007, 43, 277.
41. (d) Tretyakov, E. V.; Ovcharenko, V. I.; Sagdeev, R. Z.; Stass, D. V.; Romanenko, G. V.; Mareev, A. V.: Medvedeva, A. S. Russ. Chem. Bull; Int. Ed. 2007, 56, 2043.
42. (a) Raczvnska. E. D.; Kosinska, W.; Osmialowski. B.; Gawineck. R. Chem. Rev. 2005, 105, 3561.
43. (b) Popov, S. A.; Andreev, R. V.; Romanenko, G. V.; Ovcharenko. V. I.; Reznikov. V. A. J. Mol. Struct. 2004, 697. 49.
44. Desai. B.; Danks, T. N.; Wagner, G. Dalton Trans. 2004, 166.
45. Allen, F. H.: Kennard. O.: Watson. D. G.: Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc, Perkin Trans. 2 1987, S1.
46. (a) Bokach, N. A.; Kukushkin, V. Yu.; Haukka, M.; da Silva, J. J. R. F.; Pombeiro, A. J. L. Inorg. Chem. 2003, 42, 3602.
47. (b) Makarycheva-Mikhailova, A. V.; Bokach, N. A.; Kukushkin, V. Yu.; Kelly, P. F.; Gilby, L. M.; Kuznetsov, M. L.; Holmes, K. E.; Haukka, M.; Parr, J.; Stonehouse, J. M.; Elsegood, M. R. J.; Pombeiro, A. J. L. Inorg. Chem. 2003, 42, 301.
48. (c) Makarycheva-Mikhailova, A. V.; Haukka, M.; Bokach, N. A.; Garnovskii. D. A.; Galanski, M.; Keppler. B. K.; Pombeiro. A. J. L.; Kukushkin, V. Yu. New J. Chem. 2002, 26, 1085.
49. (a) Michelin, R. A.; Mozzon, M.; Berin, P.; Bertani, R.; Benetollo. F.; Bombieri, G.; Angelici, R. J. Organometallics 1994, 13, 1341.
50. (b) Michelin, R. A.; Belluco, U.; Mozzon, M.; Berin, P.; Bertani, R.; Benetollo, F.; Bombieri, G.; Angelici, R. J. Inorg. Chim. Acta 1994, 220, 21.
51. (c) Michelin. R. A.; Mozzon, M.; Bertani, R.; Benetollo. F.; Bombieri. G.; Angelici, R. J. Inorg. Chim. Acta 1994, 222, 327.
52. Anderson, G. K.; Davies, J. A.; Schoeck, D. J. Inorg. Chim. Acta 1983, 76, L251.
53. (a) Sustmann. R. Tetrahedron Lett. 1971. 2717. (b) Sustmann. R. Tetrahedron Lett. 1971, 2721.
54. Gas-phase AG‡ values calculated at the B3LYP/6-31G* level of theory are compared.
55. Bovd. G. V. Prog. Heterocycl. Chem. 1994, 6. 190.
56. (a) Nishiwaki, T. Synthesis 1975, 1, 20.
57. (b) Takeuchi, Y.; Furusaki, F. Adv. Heterocycl. Chem. 1977, 21, 207.
58. (c) Kashima. Ch. Heterocycles 1979, 12, 1343.
59. (d) Baraldi, P. G.: Barco. A.: Benetti, S.; Pollim, G. P.: Simoni, D. Synthesis 1987, 10, 857.
60. Coley, H. M.; Sarju, J.; Wagner. G. J. Med. Chem. 2008, .57, 135.
61. Kukushkin, V. Yu.: Oskarsson. Å: Eldmg. L. I. Inorg. Synth. 1997, 31, 279.
62. Bokach, N. A.; Pakhomova. T. B.; Kukushkin. V. Yu.; Haukka, M.; Pombeiro. A. J. L. Inorg. Chem. 2003, 42, 7560.
63. Otwinowski Z.; Minor, W. In Methods in Enzymology, Volume 276, Macromolecular Crystallography, Pan A; Carter, C. W., Sweet, J., Eds.; Academic Press: New York, 1997; pp 307-326.
64. Burla, M. C; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo. C; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 2005, 38, 381.
65. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Determination: University of Gottingen: Gottingen, Germany, 1997.
66. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837. '
67. Sheldrick, G. M. SADABS, Bruker Nonius scaling and absorption correction, v 2.10; Bruker AXS, Inc.: Madison. WI. 2003.
68. Blessing. R. H. Acta Crystallogr., Sect. A 1995, A51. 33.
69. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Gottingen: Gottingen. Germany. 1997.
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr. Stratmann, R. E.; Burant, J. C; Dapprich, S.; Millam, J. M.; Daniels, A. D, Kudin, K. N.; Strain, M. C; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M. Cammi, R.; Mennucci, B.; Pomelli, C; Adamo, C.; Clifford, S.; Ochterski. J.; Peterson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick. D. K. Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P. Komaromi, I.; Gomperts, R.; Martin. R. L.; Fox, D. J.; Keith, T.; Al-Laham. M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W. Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9. Gaussian, Inc.: Pittsburgh PA, 1998.
71. Becke. A. D. J. Chem. Phys. 1993, 98, 5648.
72. Lee, C; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
73. Andrae, D.; Haeussermann. U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123.
74. (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
75. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
76. (c) Hariharan. P. C; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
77. (a) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
78. (b) Krishnan, R.; Binklev. J. S.; Seeger, R.; Pople. J. A. J. Chem. Phys. 1980, 72, 650.
79. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
80. (b) Gonzalez, C; Schlegel, H. B. J. Cem. Phys. 1991, 95, 5853.
81. (c) Gonzalez, C; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
82. (d) Gonzalez. C; Schlegel, H. B. J.Phys. Chem. 1990, 94, 5523.
83. Tomasi. J.; Persico, M. Chem. Rev. 1997, 94, 2027.
84. Barone. V.; Cossi. M. J. Phys. Chem. 1998, 102, 1995.
85. Wiberg, K. B. Tetrahedron 1968, 24, 1083.
86. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
87. (a) Moyano. A.; Pericas, M. A.; Valentkí, E. J. Org. Chem. 1989, 54, 573.
88. (b) Lecea, B.; Arrieta, A.; Roa, G.; Ugalde. J. M.; Cossío. F. P. J. Am. Chem. Soc. 1994, 116, 9613.