Microwave-promoted reactions: Intramolecular carbanilide cyclization to hydantoins employing barium hydroxide catalyst

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3379-3382

  Gong, Young Dae ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BARIUM DERIVATIVE; CARBANILIDE; HYDANTOIN DERIVATIVE;

ARTICLE; CROSS LINKING; CYCLIZATION; DRUG SYNTHESIS; MICROWAVE RADIATION; MOLECULAR INTERACTION;

EID: 0032555024     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00497-3     Document Type: Article

References (24)

1. (a) Ware, E. Chem. Rev. 1950, 46, 403.
2. (b) Spinks, A.; Waring, W. S. Prog. Med. Chem. 1963, 3, 313.
3. (c) Karolakwojociechowska, J.; Kwiatkowaki, W.; Kieckono, K. Pharmazie 1995, 50, 114.
4. (d) Brouillette, W. J.; Jestkov, V. P.; Brown, M. L.; Akhtar, M. S. J. Med. Chem. 1994, 37, 3289.
5. (e) Brouillette, W. J.; Brown, G. B.; Deloreg, T. M.; Liang, G. J. Pharm. Sci. 1990, 79, 871.
6. Mappes, C. J.; Pommer, E.H.; Rentzea, C.; Zeeh, B. U.S. Patent 1980, 4,198,423.
7. Ohta, H.; Jikihara, T.; Wakabayashi, K.; Fujita, T. Pestic. Biochem. Physiol. 1980, 14, 153.
8. Najdi S.; Park, K.-E.; Olmsted, M. M.; Kurth, M. J. Tetrahedron Letters 1998 39, 1685.
9. Gong, Y.-D.; Najdi, S.; Olmsted, M. M.; Kurth, M. J. Unpublished results.
10. (a) Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945.
11. (b) Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Lakerge, L.; Roussel, J. O. Tetrahedron Lett. 1986, 27, 279.
12. Mingos, D.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
13. Cablewsky, T.; Faux, F. A.; Strauss, C. R. J. Org. Chem. 1994, 59, 3408.
14. (a) Kingston, H. M.; Haswell, S. J. Microwave-Enhanced Chemistry; A.C.S.: 1997, pp 455-505.
15. (b) Raner, K. D.; Strauss, C. R.; Trainor, R. W. J. Org. Chem., 1995, 60, 2456.
16. (c) Banik, B. K.; Manhas, M. S.; Kaluza, Z.; Barakat, K. J.; Bose, A. K. Tetrahedron Lett., 1992, 33, 3603.
17. (d) Abramovitch, R. A.; Abramovitch, D. A.; Iyanar, K.; Tamareselvy, K. Tetrahedron Lett., 1991, 32, 5251.
18. (e) Gedye, R. N.; Rank, W.; Westaway, K. C. Can. J. Chem., 1991, 69, 706.
19. (f) Berlan, J.; Giboreau, P.; Lefeuvre, S.; Marchand, C. Tetrahedron Lett., 1991, 32, 2363.
20. (g) Chen, S. T.; Chiou, S. H.; Wang, K. T. J. Chem. Soc., Chem. Commun., 1990, 807.
21. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Raju, V. S.; Tabei, K.; Urbanczyk-Lipkowska, Z. Heterocycles, 1990, 30, 741.
22. MICROWELL10 REACTOR consists of a μW control unit (0-500W), a time control unit (0-100 min), and a power supply (600W).
23. In order to maximize kinetic product 4a, this reaction was quenched prior to complete consumption of starting material 2a.
24. 2 in DMF provides the best conditions for this intramolecular carbanilide cyclization under μw mediation.