The first aza-Wittig reaction of the β-lactam carbonyl group

Synlett

Volumn , Issue 11, 1998, Pages 1288-1290

  Alajarín, Mateo ^a   Molina, Pedro ^a   Vidal, Ángel ^a   Tovar, Fulgencio ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042252487     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1920     Document Type: Article

References (23)

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2. b) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197;
3. c) Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209;
4. d) Barluenga J.; Palacios, F. Org. Prep. Proced. Int. 1991, 23, 1;
5. e) Gusar, N. I. Russ. Chem. Rev. (Engl. Transl.) 1991, 60, 146.
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7. Molina, P.; Alajarín, M.; López-Leonardo, C.; Madrid, I.; Foces-Foces, C.; Cano, F. H. Tetrahedron 1989, 45, 1823;
8. Molina, P.; Alajarín, M.; Vidal, A.; Elguero, J.; Claramunt, R. M. Tetrahedron 1988, 44, 2249;
9. Gololobov, Y. G.; Gusar, N. I.; Chaus, M. P. Tetrahedron 1985, 41, 793;
10. Plitsch, W.; Mukidjam, E. Chem. Ber. 1979, 112, 3577.
11. L'abbé, G.; Sorgeloos, D.; Toppet, S. Tetrahedron Lett. 1982, 23, 2909;
12. Marchand-Brynaert, J.; Ghosez, L. In Recent Progress in the Chemical Synthesis of Antibiotics, Lukacs, G. and Ohno, M., Eds.; Springer-Verlag: Berlin, 1990, p 733.
13. a) Alajarín, M.; Molina, P.; Vidal, A. Tetrahedron Lett. 1996, 37, 8945;
14. b) Alajarín, M.; Molina, P.; Vidal, A.; Tovar, F. Tetrahedron 1997,53, 13449.
15. Chmielevvski, M.; Kaluza, Z.; Abramski, W.; Belzecki, C. Tetrahedron Lett. 1987, 28, 3035.
16. See for instance; Sakurai, O.; Ogiku, T.; Takahashi, M.; Hayashi, M.; Yamanaka, T.; Horikawa, H.; Iwasaki, T. J. Org. Chem. 1996, 61, 7889.
17. Alajarín, M.; López-Lázaro, A.; Vidal, A.; Berná, J. Chem. Eur. J., in press.
18. 2: C, 65.75; H, 4.14; N, 19.17. Found: C, 65.87; H, 4.03; N, 19.34.
19. Compound 2c has been previously prepared by us through a different methodology, see ref. 5b.
20. Typical Experimental Procedure for the Preparation of Azeto[2,1-b]quinazolines and Azeto[2,1-b]quinazolin-8-ones 2. To a solution of the 2-azetidinone 1 (1 mmol) in dry toluene (15 ml) trimethylphosphane was added (1.0 ml of a 1 M toluene solution), and the mixture was stirred at room temperature until the evolution of nitrogen ceased (5-10 min). Then the solution was heated at reflux temperature for 12-24 h. After cooling, the solvent was removed under reduced pressure and the resulting material was chromatographed (silica gel; elution with n-hexane/EtOAc).
21. 3: C, 62.60; H, 4.38; N, 12.17. Found: C, 62.74; H, 4.23; N, 12.23.
22. 4) δ 36.0.
23. 3 carbon atoms of the β-lactam ring during the base-catalysed N-acylation step, probably through the intermediacy of the azetone A. (Chemical Equation Presented) It is well known that 4-acyloxy-β-lactams are configurationally unstable under basic conditions (Kametani, T.; Honda, T.; Nakayama, A.; Sasaki, Y.; Mochizuki, T.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 2228 and references therein).