An improved synthesis for the preparation of 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides has been developed. This facile two-step procedure fromα-amino acid esters and chlorosulfonyl isocyanate results in excellent yields of products.

References and Notes

1a W. C. Groutas, R. Kuang and R. Venkataraman, Biochem. Biophys. Res. Comm., 194, 341 (1994)
10.1006/bbrc.1994.1048
Web of Science® Google Scholar
1b B. Unterhalt and G. A. Hanewacker, Arch. Pharm., 321, 375 (1988).
10.1002/ardp.19883210617
CAS Web of Science® Google Scholar
2 G. W. Muller and G. E. DuBois, J. Org. Chem., 54, 4471 (1989).
10.1021/jo00279a044
CAS Web of Science® Google Scholar
3 H. J. Sanders, Chem. Eng. News, 20 (1981).
Google Scholar
4a H. R. Henze and L. M. Long, J. Am. Chem. Soc., 63, 1941 (1941)
10.1021/ja01852a042
CAS Google Scholar
4b H. R. Henze and R. J. Speer, J. Am. Chem. Soc., 64, 522 (1942)
10.1021/ja01255a014
CAS Web of Science® Google Scholar
4c H. R. Henze and A. F. Isbell, J. Am. Chem. Soc., 76, 4152 (1954).
10.1021/ja01645a029
CAS Web of Science® Google Scholar
5 P. D. Skelly, W. J. Ray and J. W. Timberlake, J. Org. Chem., 50, 267 (1985).
10.1021/jo00202a021
CAS Web of Science® Google Scholar
6 J. R. Rachele, J. Org. Chem., 28, 2898 (1963).
10.1021/jo01045a515
CAS Web of Science® Google Scholar
7 C. H. Lee, J. D. Korp and H. Kohn, J. Org. Chem., 54, 3077 (1989).
10.1021/jo00274a023
CAS Web of Science® Google Scholar
8a J. N. Coker, W. L. Kohlhase, A. O. Rogers and G. G. Allan, J. Org. Chem., 84, 3077 (1962)
Google Scholar
8b D. D. I. Ugi, Angew, Chem. Int. Ed. Engl., 1, 8 (1962).
10.1002/anie.196200081
Google Scholar
9 J. W. Timberlake, W. J. Ray, E. D. Stevens and C. L. Klein, J. Org. Chem., 54, 5824 (1989).
10.1021/jo00285a035
CAS Web of Science® Google Scholar
10a G. M. Atkins and E. M. Burgess, J. Am. Chem. Soc., 94, 6135 (1972)
10.1021/ja00772a035
CAS PubMed Web of Science® Google Scholar
10b G. M. Atkins and E. M. Burgess, J. Am. Chem. Soc., 90, 4745 (1968)
10.1021/ja01019a052
CAS Web of Science® Google Scholar
10c E. M. Burgess and W. M. Williams, J. Org. Chem., 38, 1249 (1973)
10.1021/jo00946a051
CAS Web of Science® Google Scholar
10d E. M. Burgess and W. M. Williams, J. Am. Chem. Soc., 94, 4386 (1972)
10.1021/ja00767a082
CAS Web of Science® Google Scholar
10e J. A. Kloek and K. L. Leschinsky, J. Org. Chem., 44, 305 (1979)
10.1021/jo01316a036
CAS Web of Science® Google Scholar
10f G. M. Atkins and E. M. Burgess, J. Am. Chem. Soc., 89, 2502 (1967).
10.1021/ja00986a058
CAS PubMed Web of Science® Google Scholar
11a B. Tao, Ph. D. Dissertation, University of New Orleans, 1997;
Google Scholar
11b T. A. Dobson, M. A. Davis, A. M. Hartung and J. M. Manson, Can. J. Chem., 46, 2843 (1968)
10.1139/v68-470
CAS Web of Science® Google Scholar
11c S. Selman and J. F. Eastham, J. Org. Chem., 30, 3804 (1965).
10.1021/jo01022a048
CAS Web of Science® Google Scholar
12 W. G. Kofron and L. M. Baclawski, J. Am. Chem. Soc., 47, 2002 (1925).
10.1021/ja01684a032
CAS Google Scholar

Citing Literature

Volume37, Issue4

July/August 2000

Pages 773-777

An improved procedure for the synthesis of 4,4-disubstituted-3-oxo-1,2,5-thiadiazolidine 1,1 -dioxides

Abstract

References and Notes

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

An improved procedure for the synthesis of 4,4-disubstituted-3-oxo-1,2,5-thiadiazolidine 1,1 -dioxides

Abstract

References and Notes

Citing Literature

References

Related

Information