Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3599-3602

  Muccioli, Giulio G ^a   Wouters, Johan ^b,d   Poupaert, Jacques H ^a   Norberg, Bernadette ^b   Poppitz, Wolfgang ^c   Scriba, Gerhard K E ^c   Lambert, Didier M ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF NAMUR   (Belgium)

^c FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^d IRMW   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BENZHYDRYL DERIVATIVE; CARBANILAMIDE DERIVATIVE; HYDANTOIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0142011140     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035282x     Document Type: Article

References (22)

1. Muccioli, G. G.; Poupaert, J. H.; Wouters, J.; Norberg, B.; Poppitz W.; Scriba, G. K. E.; Lambert, D. M. Tetrahedron 2003, 59, 1301-1307.
2. (a) Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Labege, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279-282.
3. (b) Gedye, R.; Smith, F.; Westaway, K. Can. J. Chem. 1987, 66, 17-26.
4. Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945-4948.
5. Two interesting reviews dealing with microwave-assisted chemistry are: Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406-416. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 571, 9225-9283.
6. Two interesting reviews dealing with microwave-assisted chemistry are: Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406-416. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 571, 9225-9283.
7. (a) Kappe, O. C.; Kumar, D.; Varma, R. S. Synthesis 1999, 10, 1799-1803.
8. (b) Paul, S.; Gupta, M.; Gupta, R.; Loupy, A. Synthesis 2002, 1, 75-78.
9. (c) Campbell, L. J.; Borges, L. F.; Heldrich, F. J. Bioorg. Med. Chem. Lett. 1994, 4, 2627-2630.
10. (d) Stadler A.; Kappe, C. O. J. Chem. Soc., Perkin Trans. 2 2000, 1363-1368.
11. (a) Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. S.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968-6970.
12. (b) Banik, B. K.; Manhas, M. S.; Kaluza, Z.; Barakat, K. J.; Bose, A. K. Tetrahedron Lett. 1992, 33, 3603-3606.
13. (c) Bose, A. K.; Jayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 37, 6989-6992.
14. (d) Bose, A. K.; Manhas, M. S.; Ganguly, S. N.; Sharma, A. H.; Banik, B. K. Synthesis 2002, 1578-1591.
15. Also termed 3,5,5′-triphenylimidazolidine-2,4-dione.
16. Henneuse, C.; Boxus, T.; Tesolin, L.; Pantano, G.; Marchand-Brynaert, J. Synthesis 1996, 4, 495-501.
17. Schramm, H. W. Sci. Pharm. 1991, 59, 115-122.
18. General Procedure for the Microwave-Assisted Method. To a solution of 3 g of benzil (14.3 mmol) and 1.94 g of phenylurea (28.6 mmol) in 25 mL of DMSO was added 25 mL of 1.2 M aqueous KOH under stirring. Following an initial 90 s, 750W microwave irradiation, the mixture was stirred for 5 min. Additional 30 s pulses were applied at 6, 9, 12, 15, 18, 21, 24, 30 min. Between pulses the mixture was stirred. After the completion of the sequence, the mixture was poured onto cold water, the resulting precipitate was filtered, dried, and recrystallized from a suitable solvent. All microwave irradiations were carried out in an open system.
19. General Procedure for the Classical Method. As used for 9, but the reacting mixture was refluxed over a period of 4 h instead of receiving the microwave pulse sequence.
20. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Raju, V. S.; Tabei, K.; Urbanczyk-Lipokwska, Z. Heterocycles 1990, 30, 741-744.
21. Also termed 3,5,5′-triphenyl-2-thio-hydantoin.
22. Hayward, R. C. J. Chem. Educ. 1983, 60, 512.