One-pot conversion of α-ureido and α-thioureido esters to imidazol-2-ones and imidazole-2-thiones

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 521-522

  Markwalder, Jay A ^a   Pottorf, Richard S ^a   Seitz, Steven P ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000775517     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6138     Document Type: Article

References (18)

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3. For other routes to imidazolones and imidazolthiones see: McCombie, H.; Scarborough, H. J. Chem. Soc. 1913, 103, 56;
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5. Anschutz, R.; Schwickerath, K. Ann. 1894, 284, 9;
6. Aoyama, H.; Sakamoto, M.; Ohnota, M.; Omote, Y. Chem. Lett. 1983, 1905;
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11. 4/HOAc: Robertson, A. D.; Martin, G. R.; Buckingham, J. S. European Patent Application EP 0313397 A1, 29 April 1989;
12. 4: Cortes, S.; Kohy, H. J. Org. Chem. 1983, 48, 2246.
13. Otter, B. A.; Falco, E. A.; Fox, J. J. J. Org. Chem. 1969, 34, 2636.
14. 4 reduction of the N-butyl ureide of norleucine N-methyl-N-methoxy amide has been reported: Reitz, D. B.; Manning, R. E. U. S. Patent 5,087,634. 11 February 1992.
15. 2R″ of the appropriate α-amino ester.
16. 1H NMR, and HRMS or combustion data consistent with the proposed structures.
17. Carini, D. J.; Duncia, J. V.; Aldrich, P. E.; Chiu, A. T.; Johnson, A. L.; Pierce, M. E.; Price, W. A.; Santella, J. B., III; Wells, G. J.; Wexler, R. R.; Wong, P. C.; Yoo, S.-E.; Timmermans, P. M. W. M. J. Med. Chem. 1991, 34, 2525.
18. +, 203.1180; Found, 203.1184. In many cases no purification is required as the product obtained is greater than 95% homogeneous.