Mesoionic pyridopyrimidinylium and pyridooxazinylium olates and non-mesoionic pyridopyrimidinones. Structures in the solid state, solution, and matrices

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 10, 2000, Pages 2096-2108

  Plüg, Carsten ^a   Wallfisch, Bianca ^a   Andersen, Heidi Gade ^a   Bernhardt, Paul V ^a   Baker, Lisa Jane ^a   Clark, George R ^a   Wong, Ming Wah ^a   Wentrup, Curt ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; HYDROGEN BONDS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

DENSITY FUNCTIONAL THEORY; PYRIDOOXAZINYLIUM OLATES; PYRIDOPYRIMIDINONES; PYRIDOPYRIMIDINYLINIUM; TAUTOMERS; ZWITTERIONIC CHARACTER;

ORGANIC COMPOUNDS;

EID: 0034309273     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003933k     Document Type: Article

References (76)

1. A. E. Tschitschibabin, Ber. Dtsch. Chem. Ges., 1924, 57, 1168.
2. W. Friedrichsen, T. Kappe and A. Böttcher, Heterocycles, 1982, 19, 1083
3. T. Kappe, Lect. Heterocycl. Chem., 1984, 7, 107.
4. (a) A. R. Katritzky and A. J. Waring, J. Chem. Soc., 1962, 1544
5. (b) A. R. Katritzky, F. D. Popp and A. J. Waring, J. Chem. Soc. B, 1966, 565.
6. R. Urban, M. Grosjean and W. Arnold, Helv. Chim. Acta, 1970, 53, 905.
7. N. Thorup and O. Simonsen, Acta Crystallogr., Sect. C, 1985, 41, 472
8. O. Simonsen, Acta Crystallogr., Sect. C, 1986, 42, 573.
9. A. Fiksdahl, C. Plüg and C. Wentrup, J. Chem. Soc., Perkin Trans. 2, 2000, 1841.
10. (a) T. Kappe and W. Lube, Monatsh. Chem., 1971, 102, 781
11. T. Kappe and W. Lube, Chem. Ber., 1979, 112, 3424
12. T. Kappe, Y. Ravai and W. Stadlbauer, Monatsh. Chem., 1983, 114, 227
13. (c) W. Friedrichsen, T. Kappe and A. Böttcher, Heterocycles, 1982, 19, 1083.
14. (a) T. Kappe, W. Golser, M. Hariri and W. Stadlbauer, Chem. Ber., 1979, 112, 1585
15. (b) W. Friedrichsen, E. Kujath and G. Liebezeit, Z. Naturforsch., Teil B, 1982, 37, 222.
16. K. T. Potts and M. Sorm, J. Org. Chem., 1971, 36, 8.
17. H. Gotthard and C. Flosbach, Chem. Ber., 1988, 121, 951.
18. 13C-NMR-Spektroskopie, Thieme, Stuttgart, 1984.
19. 13C NMR data for pyridinium ylides are taken from, K. Matsumoto, M. Ciobanu, K. Aoyama and T. Uchida, Heterocycl. Commun., 1997, 3, 499
20. K. Matsumoto, H. Katsura, T. Uchida, K. Aoyama and T. Machiguchi, Heterocycles, 1997, 45, 2443.
21. X. Ye, J. Andraos, H. Bibas, M. W. Wong and C. Wentrup, J. Chem. Soc., Perkin Trans. 1, 2000, 401.
22. A. J. Kirby, I. V. Komarov, P. D. Wothers and N. Feeder, Angew. Chem., Int. Ed., 1998, 37, 785.
23. I. Couturier-Tamburelli, J.-P. Aycard, M. W. Wong and C. Wentrup, J. Phys. Chem. A, 2000, 104, 3466.
24. C. Kratky and T. Kappe, J. Heterocycl. Chem., 1981, 18, 881.
25. T. Debaerdemaker and W. Friedrichsen, Z. Naturforsch., Teil B, 1982, 37, 217.
26. T. Kappe, W. Lube, K. Thonhofer, C. Kratky and U. G. Wagner, Heterocycles, 1995, 40, 681.
27. H. Bibas, C. H. L. Kennard and C. Wentrup, unpublished data.
28. R. Bossio, S. Marcaccini, R. Pepino and P. Paoli, J. Heterocycl. Chem., 1993, 30, 33.
29. C. Donati, W. K. Janowski, R. H. Prager, M. R. Taylor and L. M. Vilkins, Aust. J. Chem., 1989, 42, 2161.
30. H. Song, H.-S. Shin, K.-I. Park and S. I. Cho, Acta Crystallogr., Sect. C, 1998, 54, 1915
31. M. Balogh, I. Hermecz, G. Naray-Szabo, K. Simon and Z. Meszaros, J. Chem. Soc., Perkin Trans. 1, 1986, 753
32. M. P. Gupta and K. Banerjee, Acta Crystallogr., Sect. B., 1982, 2947
33. H. L. Ammon and G. L. Wheeler, Acta Crystallogr., Sect. B, 1974, 30, 1146.
34. G. G. Qiao, J. Andraos and C. Wentrup, J. Am. Chem. Soc., 1996, 118, 5634
35. P. Visser, R. Zuhse, M. W. Wong and C. Wentrup, J. Am. Chem. Soc., 1996, 118, 12598.
36. W. H. De Camp and J. M. Stewart, J. Heterocycl. Chem., 1970, 7, 895
37. O. Gerulat, G. Himbert and U. Bergsträsser, Synlett, 1995, 835.
38. W. E. Thiessen and H. Hope, J. Am. Chem. Soc., 1967, 89, 5977
39. H. Hope and W. E. Thiessen, Acta Crystallogr., Sect. B, 1969, 25, 1237
40. T. J. King, P. N. Preston, J. S. Suffolk and K. Turnbull, J. Chem. Soc., Perkin Trans. 2, 1979, 1751
41. S. Nespurek, J. Hasek, M. Sorm and K. Huml, J. Mol. Struct., 1982, 82, 95
42. J. Hasek, P. T. Beurskens, J. Obrda, S. Nespurek, H. Schenk, K. Goubitz, K. Huml and J. D. Schagen, Coll. Czech. Chem. Commun., 1986, 50, 1764
43. C.-H. Ueng, P. L. Lee, Y. Wang and M.-Y. Yeh, Acta Crystallogr., Sect. C, 1985, 41, 1776
44. C.-H. Ueng, Y. Wang and M. Y. Yeh, Acta Crystallogr., Sect. C, 1987, 43, 1122.
45. G. V. Boyd, C. G. Davies, J. D. Donaldson, J. Silver and P. H. Wright, J. Chem. Soc., Perkin Trans. 2, 1975, 1280
46. P. L. Toupet, F. Texier and R. Carrié, Acta Crystallogr., Sect. C, 1991, 47, 328.
47. Data for 3-propionyl- and 3-acetyl[1,3]oxazolo[2,1b]pyridin-4-ylium- 2-olate 24 and 2-(tert-butyl)-3-methyl-4-(trifluoroacetyl)-munchnone 25: C. Plüg and C. Wentrup, unpublished results.
48. S. Nespurek, S. Böhm and J. Kuthan, J. Mol. Struct. (THEOCHEM), 1986, 136, 261
49. K. Undheim, M. A. F. El-Gendy and T. Hurum, Org. Mass Spectrom., 1974, 9, 1242
50. E. Funke and R. Huisgen, Chem. Ber., 1971, 104, 3222
51. J. Lukac and H. Heimgartner, Helv. Chim. Acta, 1979, 62, 1236
52. W. Friedrichsen and W.-D. Schröer, Liebigs Ann. Chem., 1980, 1836.
53. N. Harrit, A. Holm, I. R. Dunkin, M. Poliakoff and J. J. Turner, J. Chem. Soc., Perkin Trans. 2, 1987, 1227.
54. Ring-chain isomerism between 1-isocyanatocarbonylpyrazole and the pyrazolo[1,2-a][1,2,4]triazolyliumolate has been reported: A. Böttcher, T. Debaerdemaeker, J. G. Radziszewski and W. Friedrichsen, Chem. Ber., 1988, 121, 895.
55. For other ring-chain isomerizations involving isothiocyanates, see R. M. Moriarty, R. Mukherjee, O. L. Chapman and D. R. Eckroth, Tetrahedron Lett., 1971, 397
56. S. Chaloupka, H. Heimgartner, H. Schmid, H. Link, P. Schönholzer and K. Bernauer, Helv. Chim. Acta, 1976, 59, 2566.
57. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapparich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challocombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98, Gaussian, Inc., Pittsburgh PA, 1998.
58. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648
59. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B: Condens. Matter Mater., 1988, 37, 785.
60. (a) M. W. Wong, M. J. Frish and K. B. Wiberg, J. Am. Chem. Soc., 1991, 113, 4776
61. (b) M. W. Wong, K. B. Wiberg and M. J. Frisch, J. Chem. Phys., 1991, 95, 8991.
62. K. B. Wiberg, T. A. Keith, M. J. Frisch and M. Murcko, J. Phys. Chem., 1995, 99, 7702.
63. J. R. Cheeseman, G. W. Trucks, T. Keith and M. J. Frisch, J. Phys. Chem., 1996, 104, 5497.
64. M. W. Wong, Chem. Phys. Lett., 1996, 256, 391.
65. A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899.
66. H. L. Ammon and G. L. Wheeler, Acta Crystallogr., Sect. B, 1974, 30, 1146
67. S. Salishi, J. L. Brianso, X. Solans and M. Front-Altaba, Acta Crystallogr., Sect. C, 1985, 41, 474
68. M. P. Gupta and K. Banerjee, Acta Crystallogr., Sect. B, 1982, 38, 2947.
69. The XTAL3.2 User's Manual, eds. S. R. Hall, H. D. Flack and J. M. Stewart, Universities of Western Australia, Geneva and Maryland, 1992.
70. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467.
71. G. M. Sheldrick, SHELXL-97: Program for Crystal Structure Determination, University of Göttingen, 1997.
72. A. L. Spek, Acta Crystallogr., Sect. A, 1990, 46, C34.
73. P. Dvortsak, G. Resofszki, L. Zalantai and A. I. Kiss, Tetrahedron, 1976, 32, 2117.
74. C. Plüg, W. Frank and C. Wentrup, J. Chem. Soc., Perkin Trans 2, 1999, 1087.
75. G. Roma, M. Di Braccio, G. Leoncini and B. Aprile, Farmaco, 1993, 48, 1225.
76. H. G. Andersen and C. Wentrup, unpublished results.