Reductive dehalogenation of 4-halogenomethyl azetidin-2-one derivatives. Synthesis of (4-oxo-azetidin-2-yl)acetonitriles

Journal of Chemical Research

Volumn , Issue 8, 2004, Pages 558-563

  Boros, Éva ^a   Bertha, Ferenc ^a   Fetter, József ^a   Vida, László ^a   Kajtár Peredy, Mária ^b   Czira, Gábor ^c  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c GEDEON RICHTER LTD   (Hungary)

Author keywords

(4 oxo azetidin 2 yl)acetonitriles; Azetidinones; Reductive dehalogenation; lactam ring cleavage

Indexed keywords

(4 OXOAZATIDIN 3 YL)ACETONITRILE; ACETONITRILE; AZETIDINONE DERIVATIVE; BETA LACTAM ANTIBIOTIC; OLIGOPEPTIDE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DEHALOGENATION; DERIVATIZATION; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

EID: 7644239902     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234042563848     Document Type: Article

References (21)

1. I. Ojima, S. Suga and R. Abe, Chem. Lett., 1980, 853.
2. N. Hatanaka and I. Ojima, Chem. Lett., 1981, 231.
3. T. Yoshioka, T. Tsuchida, H. Tone and R. Okamoto, Eur. Patt. Appl., 10. 04. 1991, EP 0 421 440 A2.
4. B. K. Banik, K. J. Barakat, D. R. Wagle, M. S. Manhas and A. K. Bose, J. Org. Chem., 1999, 64, 5746.
5. G. Gunda and T. Durst, J. Org. Chem., 1983, 48, 2092.
6. Gy. Simig, J. Fetter, Gy. Hornyák, K. Zauer and G. Doleschall, Acta Chim. Hung., 1985, 119, 1, 17.
7. Z. Tombor, Z. Greff, J. Nyitrai and M. Kajtár-Peredy, Liebigs Ann. Org. Bioorg. Chem, 1995, 5, 825.
8. K. Hignett, J. Soc. Chem. Ind. London, 1935, 54, 98.
9. H. Fritz, J. Lehmann and P. Schlesselmann, Carbohydr. Res., 1983, 113, 71.
10. J. Fetter, E. Keskeny, T. Czuppon, K. Lempert, M. Kajtár-Peredy and J. Tamás, J. Chem. Soc. Perkin Trans. 1., 1992, 3061.
11. G. Le Thanh, J. Fetter, K. Lempert, M. Kajtár-Peredy and Á. Gömöry, Tetrahedron, 1996, 52, 30, 10169.
12. C. Palomo, J. M. Ontoria, J. M. Odrizola, J. M. Alzpurua and I. Ganboa, J. Chem. Soc. Chem. Commun., 1990, 3, 248.
13. A. Sápi, F. Bertha, J. Fetter, M. Kajtár-Peredy, M. Gy. Keserü and K. Lempert, Tetrahedron, 1996, 52, 3, 771.
14. P. J. Garegg and B. Samuelsson, J. Chem. Soc. Chem. Commun., 1979, 978.
15. G. L. Lange and C. Gottards, Synth. Commun., 1990, 20, 1473.
16. M. P. Cooke and C. M. Pollock, J. Org. Chem., 1993, 58, 26, 7474.
17. M. Yu, Y. Zhang and C. Qian, J. Chem. Res. Synop., 1998, 5, 256.
18. S. Kano, T. Ebata and S. Shibuya, J. Chem. Soc. Perkin Trans. 1., 1980, 2105.
19. T. Kawabata, T. Minami and T. Hiyama, J. Org. Chem., 1992, 57, 6, 1864.
20. A. R. Desmukh, H. Zhang, L. duc Tran and E. Biehl, J. Org. Chem., 1992, 57, 8, 2485.
21. G. Le Thanh, J. Fetter, M. Kajtár-Peredy, K. Lempert and F. Bertha, Tetrahedron, 1999, 55, 8457.