C-3 β-lactam carbocation equivalents: versatile synthons for C-3 substituted β-lactams

Tetrahedron

Volumn 62, Issue 21, 2006, Pages 5054-5063

  Bhalla, Aman ^a   Madan, Sachin ^a   Venugopalan, Paloth ^a   Bari, Shamsher S ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

Lactam; Disubstituted lactams; Lewis acid; Monosubstituted lactams; Nucleophiles

Indexed keywords

1 (4' METHOXYPHENYL) 3 (2' FURANYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (2' METHOXYNAPHTHYL) 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (2' OXOCYCLOHEXANYL) 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (2',4' DIMETHOXYPHENYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (2',5' DIMETHOXYPHENYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (3' INDOLYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (4' HYDROXYPHENYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (4' METHOXYPHENYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 (4' METHYLPHENYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 ALLYL 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 ALLYL 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 BENZYLTHIO 4 (4' METHOXYPHENYL)AZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 CHLORO 3 BENZYLTHIO 4 (4' METHOXYPHENYL)AZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 CHLORO 3 BENZYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 CHLORO 3 PHENYLTHIO 4 (4' METHOXYPHENYL)AZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3 PHENYLTHIO 4 (4' METHOXYPHENYL)AZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3,3 BIS(4' METHOXYPHENYL) 4 (4' METHOXYPHENYL)AZETIDIN 2 ONE; 1 (4' METHOXYPHENYL) 3,3 BIS(4' METHOXYPHENYL) 4 PHENYLAZETIDIN 2 ONE; 1 BENZYL 3 (2' METHOXYNAPHTHYL) 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 BENZYL 3 (4' METHOXYPHENYL) 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 BENZYL 3 CHLORO 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 BENZYL 3 PHENYLTHIO 4 PHENYLAZETIDIN 2 ONE; 1 BENZYL 3,3 BIS(4' METHOXYPHENYL) 4 PHENYLAZETIDIN 2 ONE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; BETA LACTAM; HETEROCYCLIC COMPOUND; LEWIS ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 33745967991     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.050     Document Type: Article

References (28)

1. Durckheimer W., Blumbatch J., Lattrell R., and Scheunrmann K.H. Angew. Chem., Int. Ed. Engl. 24 (1985) 180-202
2. Chu D.T.W., Plattner J.J., and Katz L. J. Med. Chem. 39 (1996) 3853-3874
3. In: Morin R.B., and German M. (Eds). Chemistry and Biology of β-Lactam Antibiotics (1982), Academic, New York, NY
4. Burnett D.A. Tetrahedron Lett. 35 (1994) 7339-7342
5. Vaccaro D.W., and Davis Jr. H.R. Bioorg. Med. Chem. Lett. 8 (1998) 313-318
6. Han W.T., Trehan A.K., Wright J.J.K., Federici M.E., Seiler S.M., and Meanwell N.A. Bioorg. Med. Chem. 3 (1995) 1123-1143
7. Borthwick A.D., Weingarte G., Haley T.M., Tomaszewski T.M., Wang W., Hu Z., Bedard J., Jin H., Yuen L., and Mansour T.S. Bioorg. Med. Chem. Lett. 8 (1998) 365-370
8. Burnett D.A., Caplen M.A., Davis Jr. H.R., Burrie R.E., and Clader J.W. J. Med. Chem. 37 (1994) 1733-1736
9. d`Angelo J., and Pecquet-Dumas F. Tetrahedron Lett. 24 (1983) 1403-1406
10. Roe J.M., and Thomas E.J. Synlett (1990) 727-728
11. Yamashita H., Minami N., Sakakibara K., Kobayashi S., and Ohno M. Chem. Pharm. Bull. 36 (1988) 69
12. Madan S., Arora R., Venugopalan P., and Bari S.S. Tetrahedron Lett. 41 (2000) 5577-5581
13. Manhas M.S., van der Veen J.M., Wagle D.R., Hegde V.R., Bari S.S., Kosarych Z., Ghosh M., and Krishanan L. Indian J. Chem. 25B (1986) 1095-1104
14. Arai K., Ohara Y., Iizumi T., and Takakuwa Y. Tetrahedron Lett. 24 (1983) 1531-1534
15. van der Veen J.M., Bari S.S., Krishanan L., Manhas M.S., and Bose A.K. J. Org. Chem. 54 (1989) 5758-5762
16. Chu D.T.W. J. Org. Chem. 48 (1983) 3571-3573
17. Bari S.S., Venugopalan P., Arora R., Modi G., and Madan S. Heterocycles 68 (2006) in press
18. Tamura Y., Shindo H., Uneishi J., and Ishibashi M. Tetrahedron Lett. 21 (1980) 2547-2548
19. Wada M., Shigeshisa T., Kitani H., and Akiba K. Tetrahedron Lett. 24 (1983) 1715-1718
20. Paterson I., and Flemming I. Tetrahedron Lett. 20 (1979) 2179-2182
21. Flemming I. Chem. Soc. Rev. 10 (1981) 83-111
22. Borenbridge P. Synthesis (1983) 85-104
23. 2=0.1102 for 2339 reflections [I>2σ(I)]. Crystallographic data (excluding structure factors) for the structure 10a in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 292646.
24. 2=0.1011 for 3147 reflections [I>2σ(I)]. Crystallographic data (excluding structure factors) for the structure 11a in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 292647.
25. Ireland R.E., and Marshall J.A. J. Org. Chem. 27 (1962) 1615-1619
26. 2=0.1115 for 3655 reflections [I>2σ(I)]. Crystallographic data (excluding structure factors) for the structure 9j in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 292645.
27. Bari S.S., Venugopalan P., and Arora R. Tetrahedron Lett. 44 (2003) 895-897
28. 2=0.0915 for 3511 reflections [I>2σ(I)]. Crystallographic data (excluding structure factors) for the structure 9s in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 292648.