A novel procedure for the formation of isatins via carbonylation of lithiated N'-aryl-N,N-dimethylureas

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 945-947

  Smith, Keith ^a   El Hiti, Gamal A ^a,b   Hawes, Anthony C ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b Tanta University   (Egypt)

Author keywords

Carbonylation; Isatins; Lithiation; Organolithiums; Ureas

Indexed keywords

BROMINE DERIVATIVE; CARBON MONOXIDE; ISATIN DERIVATIVE; LITHIUM DERIVATIVE; METHYLUREA;

ARTICLE; DIMERIZATION; POSITRON EMISSION TOMOGRAPHY; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0032977296     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3085     Document Type: Article

References (37)

1. Trzupek, L. S.; Newirth, T. L.; Kelly, E. G.; Sbarbarti, N. E.; Whitesides, G. M. J. Am. Chem Soc. 1973, 95, 8118.
2. See for example: Seebach, D. Angew. Chem. 1969, 81, 690; Angew. Chem., Int. Ed. Engl. 1969, 8, 639; Lever, Jr. O. W. Tetrahedron 1976, 32, 1943; Beak, P.; Reitz, D. R. Chem. Rev. 1978, 78, 275.
3. See for example: Seebach, D. Angew. Chem. 1969, 81, 690; Angew. Chem., Int. Ed. Engl. 1969, 8, 639; Lever, Jr. O. W. Tetrahedron 1976, 32, 1943; Beak, P.; Reitz, D. R. Chem. Rev. 1978, 78, 275.
4. See for example: Seebach, D. Angew. Chem. 1969, 81, 690; Angew. Chem., Int. Ed. Engl. 1969, 8, 639; Lever, Jr. O. W. Tetrahedron 1976, 32, 1943; Beak, P.; Reitz, D. R. Chem. Rev. 1978, 78, 275.
5. See for example: Seebach, D. Angew. Chem. 1969, 81, 690; Angew. Chem., Int. Ed. Engl. 1969, 8, 639; Lever, Jr. O. W. Tetrahedron 1976, 32, 1943; Beak, P.; Reitz, D. R. Chem. Rev. 1978, 78, 275.
6. Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534; Seyferth, D.; Weinstein, R. M.; Wang, W.-L. J. Org. Chem. 1983, 48, 1144; Seyferth, D.; Weinstein, R. M.; Wang, W.-L.; Hui, R. C. Tetrahedron Lett. 1983, 24, 4907; Seyferth, D.; Hui, R. C. Organometallics 1984, 3, 1651.
7. Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534; Seyferth, D.; Weinstein, R. M.; Wang, W.-L. J. Org. Chem. 1983, 48, 1144; Seyferth, D.; Weinstein, R. M.; Wang, W.-L.; Hui, R. C. Tetrahedron Lett. 1983, 24, 4907; Seyferth, D.; Hui, R. C. Organometallics 1984, 3, 1651.
8. Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534; Seyferth, D.; Weinstein, R. M.; Wang, W.-L. J. Org. Chem. 1983, 48, 1144; Seyferth, D.; Weinstein, R. M.; Wang, W.-L.; Hui, R. C. Tetrahedron Lett. 1983, 24, 4907; Seyferth, D.; Hui, R. C. Organometallics 1984, 3, 1651.
9. Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534; Seyferth, D.; Weinstein, R. M.; Wang, W.-L. J. Org. Chem. 1983, 48, 1144; Seyferth, D.; Weinstein, R. M.; Wang, W.-L.; Hui, R. C. Tetrahedron Lett. 1983, 24, 4907; Seyferth, D.; Hui, R. C. Organometallics 1984, 3, 1651.
10. Nudelman, N. S.; Vitale, A. A. J. Org. Chem. 1981, 46, 4625; Seyferth, D.; Hui, R.C.; Wang, W.-L. J. Org. Chem. 1993, 58, 5843.
11. Nudelman, N. S.; Vitale, A. A. J. Org. Chem. 1981, 46, 4625; Seyferth, D.; Hui, R.C.; Wang, W.-L. J. Org. Chem. 1993, 58, 5843.
12. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
13. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
14. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
15. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
16. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
17. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
18. For other work on intramolecular trapping of acyllithiums, see Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440; Ryu, I.; Hayama, Y.; Hiria, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990,112, 7061; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533; Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634; Kai, H.; Yamauchi, M.; Murai, S. Tetrahedron Lett. 1997, 38, 9027.
19. Smith, K.; Pritchard, G. J. Angew. Chem. 1990, 102, 298; Angew. Chem. Int. Ed. Engl. 1990, 29, 282.
20. Smith, K.; Pritchard, G. J. Angew. Chem. 1990, 102, 298; Angew. Chem. Int. Ed. Engl. 1990, 29, 282.
21. Phelps, M. E.; Hoffman, E. J.; Mullani, N. A.; Ter-Pogossian, M. M. J. Nucl. Med. 1975, 22, 58.
22. Smith, K. et al., unpublished results.
23. Smith, K.; Shukla, A. P.; Matthews, I. Sulfur Lett. 1996, 20, 121.
24. See for example, Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1, 1998, 4041; Smith, K.; Anderson, D.; Matthews, I. J. Org. Chem. 1996, 61, 662; Sulfur Lett. 1995, 18, 79; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647, 656; J. Chem. Soc., Perkin Trans. 1, 1995, 1029; Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. Sulfur Lett. 1994, 17, 197.
25. See for example, Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1, 1998, 4041; Smith, K.; Anderson, D.; Matthews, I. J. Org. Chem. 1996, 61, 662; Sulfur Lett. 1995, 18, 79; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647, 656; J. Chem. Soc., Perkin Trans. 1, 1995, 1029; Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. Sulfur Lett. 1994, 17, 197.
26. See for example, Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1, 1998, 4041; Smith, K.; Anderson, D.; Matthews, I. J. Org. Chem. 1996, 61, 662; Sulfur Lett. 1995, 18, 79; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647, 656; J. Chem. Soc., Perkin Trans. 1, 1995, 1029; Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. Sulfur Lett. 1994, 17, 197.
27. See for example, Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1, 1998, 4041; Smith, K.; Anderson, D.; Matthews, I. J. Org. Chem. 1996, 61, 662; Sulfur Lett. 1995, 18, 79; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647, 656; J. Chem. Soc., Perkin Trans. 1, 1995, 1029; Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. Sulfur Lett. 1994, 17, 197.
28. See for example, Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1, 1998, 4041; Smith, K.; Anderson, D.; Matthews, I. J. Org. Chem. 1996, 61, 662; Sulfur Lett. 1995, 18, 79; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647, 656; J. Chem. Soc., Perkin Trans. 1, 1995, 1029; Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. Sulfur Lett. 1994, 17, 197.
29. See for example, Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1, 1998, 4041; Smith, K.; Anderson, D.; Matthews, I. J. Org. Chem. 1996, 61, 662; Sulfur Lett. 1995, 18, 79; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647, 656; J. Chem. Soc., Perkin Trans. 1, 1995, 1029; Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. Sulfur Lett. 1994, 17, 197.
30. 4), and evaporated under reduced pressure. The crude product obtained was purified by flash column chromatography using a 50/50 mixture of diethyl ether and light petroleum (bp 30-40 °C) to give the pure isatin. The yields obtained are recorded in Table 1.
31. Bettembourg, M.-C.; David, S. Bull. Soc. Chim. Fr, 1962, 772; David, S.; Dauct, M.-C. Bull. Soc. Chim. Fr. 1967, 2152; Franklin, C. S.; White, A. C. J. Chem. Soc. 1963, 1335; Bergman, J. Tetrahedron 1971, 27, 1167.
32. Bettembourg, M.-C.; David, S. Bull. Soc. Chim. Fr, 1962, 772; David, S.; Dauct, M.-C. Bull. Soc. Chim. Fr. 1967, 2152; Franklin, C. S.; White, A. C. J. Chem. Soc. 1963, 1335; Bergman, J. Tetrahedron 1971, 27, 1167.
33. Bettembourg, M.-C.; David, S. Bull. Soc. Chim. Fr, 1962, 772; David, S.; Dauct, M.-C. Bull. Soc. Chim. Fr. 1967, 2152; Franklin, C. S.; White, A. C. J. Chem. Soc. 1963, 1335; Bergman, J. Tetrahedron 1971, 27, 1167.
34. Bettembourg, M.-C.; David, S. Bull. Soc. Chim. Fr, 1962, 772; David, S.; Dauct, M.-C. Bull. Soc. Chim. Fr. 1967, 2152; Franklin, C. S.; White, A. C. J. Chem. Soc. 1963, 1335; Bergman, J. Tetrahedron 1971, 27, 1167.
35. Gassmann, P. G.; Cue, B. W. Jn; Luh, T.-Y. J. Org. Chem. 1977, 42, 1344.
36. 2 189.0789).
37. O'Sullivan, D. G.; Sadler, P. W. J. Chem. Soc. 1956, 2202.