An efficient synthesis of thioisomunchnones derived from uracils and uridine: Novel type of mesoionic nucleosides

Organic Letters

Volumn 2, Issue 5, 2000, Pages 581-584

  Wamhoff, Heinrich ^a   Hǒhmann, Christof ^a   Sohár, Pál ^b  

^a UNIVERSITY OF BONN   (Germany)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008651419     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990385u     Document Type: Article

References (34)

1. Reactions of Uracils, 25. For part 24, see: Wamhoff, H.; Sattler, C.; Sohár, P.; Rohonczy, J. Synth. Commun. 1999, 29, 3919-3937.
2. Duffin, G. F.; Kendall, J. D. J. Chem. Soc. 1951, 734-739.
3. Koenigs, E.; Geisler, H. Ber. Dtsch. Chem. Ges. 1924, 57, 2076-2079. Tschitschibabin, A. E.; Woroshtzov, N. N. Ber. Dtsch. Chem. Ges. 1933, 66, 364-372. Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899-900.
4. Koenigs, E.; Geisler, H. Ber. Dtsch. Chem. Ges. 1924, 57, 2076-2079. Tschitschibabin, A. E.; Woroshtzov, N. N. Ber. Dtsch. Chem. Ges. 1933, 66, 364-372. Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899-900.
5. Koenigs, E.; Geisler, H. Ber. Dtsch. Chem. Ges. 1924, 57, 2076-2079. Tschitschibabin, A. E.; Woroshtzov, N. N. Ber. Dtsch. Chem. Ges. 1933, 66, 364-372. Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899-900.
6. Padwa, A.; Harring, S. R.; Hertzog, D. L.; Nadler, W. R. Synthesis 1994, 993-1004. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141.
7. Padwa, A.; Harring, S. R.; Hertzog, D. L.; Nadler, W. R. Synthesis 1994, 993-1004. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141.
8. Review: Wamhoff, H.; Dzenis, J.; Hirota, K. Adv. Heterocycl. Chem. 1992, 55, 129-259.
9. Kaneko, K.; Katayama, H.; Wakabayashi, T.; Kumonaka, T. Synthesis 1988, 152-154.
10. 2S: C, 60.45; H, 3.90; N, 10.85; S, 12.41. Found: C, 60.06; H, 3.88; N, 10.86; S, 12.38.
11. Fox, J. J.; Van Praag, D.; Wempen, I.; Doerr, I. L.; Cheong, L.; Knoll, J. E.; Eidinoff, M. L.; Bendick, A.; Brown, G. B. J. Am. Chem. Soc. 1959, 81, 178-187.
12. + - aglycone).
13. Glennon, R. A.; Schubert, E.; Bass, R. G. Tetrahedron Lett. 1981, 22, 2753-2756. Bambury, R. E.; Feeley, D. T.; Lawton, G. C.; Weaver, J. M.; Wemple, J. J. Chem, Soc., Chem. Commun. 1984, 422-423. Schubert, E. M.; Schram, K. H.; Glennon, R. A. J. Heterocycl. Chem. 1985, 22, 889-905.
14. Glennon, R. A.; Schubert, E.; Bass, R. G. Tetrahedron Lett. 1981, 22, 2753-2756. Bambury, R. E.; Feeley, D. T.; Lawton, G. C.; Weaver, J. M.; Wemple, J. J. Chem, Soc., Chem. Commun. 1984, 422-423. Schubert, E. M.; Schram, K. H.; Glennon, R. A. J. Heterocycl. Chem. 1985, 22, 889-905.
15. Glennon, R. A.; Schubert, E.; Bass, R. G. Tetrahedron Lett. 1981, 22, 2753-2756. Bambury, R. E.; Feeley, D. T.; Lawton, G. C.; Weaver, J. M.; Wemple, J. J. Chem, Soc., Chem. Commun. 1984, 422-423. Schubert, E. M.; Schram, K. H.; Glennon, R. A. J. Heterocycl. Chem. 1985, 22, 889-905.
16. Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-22. Cf. also: Coburn, R. A. J. Heterocycl. Chem. 1971, 8, 881-887. Coburn, R. A.; Capellotti, R. A.; Glennon, R. A. J. Heterocycl. Chem. 1973, 10, 479-485.
17. Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-22. Cf. also: Coburn, R. A. J. Heterocycl. Chem. 1971, 8, 881-887. Coburn, R. A.; Capellotti, R. A.; Glennon, R. A. J. Heterocycl. Chem. 1973, 10, 479-485.
18. Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-22. Cf. also: Coburn, R. A. J. Heterocycl. Chem. 1971, 8, 881-887. Coburn, R. A.; Capellotti, R. A.; Glennon, R. A. J. Heterocycl. Chem. 1973, 10, 479-485.
19. Coburn, R. A.; Glennon, R. A. J. Heterocycl. Chem. 1973, 10, 487-494.
20. Yokoyama, M.; Ikuma, T.; Obara, N.; H. Togo, H. J. Chem. Soc., Perkin Trans, 1 1990, 3243-3247.
21. Review: Reichardt, C. Chem. Ber. 1994, 94, 2319-2358; Nachr. Chem. Techn. Lab. 1997, 45, 759-763. Solvatochromism: Hantzsch, A. Ber. Dtsch. Chem. Ges. 1922, 55, 953-979. Kosover, E. M. J. Am. Chem. Soc. 1958, 80, 3253-3270. Cf. also some own measurements on pseudocross-conjugated mesomeric betaines: Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976-6984.
22. Review: Reichardt, C. Chem. Ber. 1994, 94, 2319-2358; Nachr. Chem. Techn. Lab. 1997, 45, 759-763. Solvatochromism: Hantzsch, A. Ber. Dtsch. Chem. Ges. 1922, 55, 953-979. Kosover, E. M. J. Am. Chem. Soc. 1958, 80, 3253-3270. Cf. also some own measurements on pseudocross-conjugated mesomeric betaines: Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976-6984.
23. Review: Reichardt, C. Chem. Ber. 1994, 94, 2319-2358; Nachr. Chem. Techn. Lab. 1997, 45, 759-763. Solvatochromism: Hantzsch, A. Ber. Dtsch. Chem. Ges. 1922, 55, 953-979. Kosover, E. M. J. Am. Chem. Soc. 1958, 80, 3253-3270. Cf. also some own measurements on pseudocross-conjugated mesomeric betaines: Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976-6984.
24. Review: Reichardt, C. Chem. Ber. 1994, 94, 2319-2358; Nachr. Chem. Techn. Lab. 1997, 45, 759-763. Solvatochromism: Hantzsch, A. Ber. Dtsch. Chem. Ges. 1922, 55, 953-979. Kosover, E. M. J. Am. Chem. Soc. 1958, 80, 3253-3270. Cf. also some own measurements on pseudocross-conjugated mesomeric betaines: Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976-6984.
25. Review: Reichardt, C. Chem. Ber. 1994, 94, 2319-2358; Nachr. Chem. Techn. Lab. 1997, 45, 759-763. Solvatochromism: Hantzsch, A. Ber. Dtsch. Chem. Ges. 1922, 55, 953-979. Kosover, E. M. J. Am. Chem. Soc. 1958, 80, 3253-3270. Cf. also some own measurements on pseudocross-conjugated mesomeric betaines: Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976-6984.
26. Ishchenko, A. A.; Kachkovskii, A. D.; Romanov, N. N.; Fedotov, K. V. Ukr. Khim. Zh. 1985, 51, 987-993 [Chem. Abstr. 1986, 104, 98492a].
27. Ishchenko, A. A.; Kachkovskii, A. D.; Romanov, N. N.; Fedotov, K. V. Ukr. Khim. Zh. 1985, 51, 987-993 [Chem. Abstr. 1986, 104, 98492a].
28. Cf. Ramsden, C. A. In Comprehensive Organic Chemistry, Vol. 4; Barton D. H. R., Sammes, P. G., Eds.; Pergamon Press: Oxford, 1979; pp 1171-1228.
29. Potts, K. T.; Houghton, E.; Singh, K. P. J. Org. Chem. 1974, 39, 3627-3631. Potts, K. T.; Bordeaux, K. G.; Kuehnling, W. R.; Salsbury, R. L. J. Org. Chem. 1985, 50, 1666-1676.
30. Potts, K. T.; Houghton, E.; Singh, K. P. J. Org. Chem. 1974, 39, 3627-3631. Potts, K. T.; Bordeaux, K. G.; Kuehnling, W. R.; Salsbury, R. L. J. Org. Chem. 1985, 50, 1666-1676.
31. + - aglycon). A complete purification could not be achieved, as each chromatography leads to a partial decomposition of the product.
32. Wamhoff, H.; Wald, K.Org. Prep. Proced. Int. 1975, 7, 251-253; Chem. Ber. 1977, 110, 1699-1715.
33. Wamhoff, H.; Wald, K.Org. Prep. Proced. Int. 1975, 7, 251-253; Chem. Ber. 1977, 110, 1699-1715.
34. 4ClN 125.0033, found 125.0035.