Formation and Cyclization of Acyl Thioamides. A Novel β-Lactam Forming Process

Journal of the American Chemical Society

Volumn 117, Issue 21, 1995, Pages 5859-5860

  Creary, Xavier ^a   Zhu, Chen ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

EID: 0029053052     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00126a029     Document Type: Article

References (17)

1. Seebach, D.; Lubosch, W.; Enders, D. Chem. Ber. 1976, 109, 1309.
2. Seebach, D.; Lubosch, W.; Enders, D. Angew. Chem., Int. Ed. Engl. 1973, 12, 1014.
3. Banhidai, B.; Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1973, 12, 836.
4. Lien, M. H.; Ablenas, F. J.; George, B. E.; Maleki, M.; Jain, R.; Hopkinson, A. C. Can. J. Chem. 1987, 65, 1800.
5. Creary, X.; Hatoum, M. N.; Barton, A.; Aldridge, T. E. J. Org. Chem. 1992, 57, 1887.
6. Ramon, D. J.; Yus, M. Tetrahedron Lett. 1993, 34, 7115.
7. Previously, certain acyl thioamides have been prepared by reaction of ketones RCOCH3 with SOCI2 followed by reaction with secondary amines. See: Adiwidiaja, G.; Günther, H.; Voss, J. Liebigs Ann. Chem. 1983, 1116.
8. For leading references, see: Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
9. Seebach, D.; Lubosch, W. Angew. Chem., Int. Ed. Engl. 1976, 15, 313.
10. Lubosch, W.; Seebach, D. Helv. Chim. Acta 1980, 63, 102.
11. Kowalski, C.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978, 43, 2601.
12. Kochhar, K. S.; Cottrell, D. A.; Pinnick, H. W. Tetrahedron Lett. 1983, 24, 1323.
13. Zwanenburg, B.; Janssen, W. A. J. Synthesis 1973, 617.
14. Nilsson, N. H.; Jacobsen, C.; Sϕrensen, O. N.; Haunsϕe, N. K.; Senning, A. Chem. Ber. 1972, 105, 2854.
15. 2. See: Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958 and references therein.
16. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
17. Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1–3.