Abstract
The stability of the β-lactam ring under reductive conditions was examined in order to find a selective method for the synthesis of (4-oxo-azetidin-2-yl)acetonitrile derivatives. Fifteen variously substituted 4-halogenomethyl-β-lactam derivatives were synthesised and dehalogenated by three reductive methods. It was found that both the substituents connected to the four-membered ring and to the halogenomethyl group, as well as the applied method have considerable influence on the ratio of the resulting ring-containing and ring-opened products. The best conditions have been defined to give – state products – in excellent yields.
Keywords
References
1.
Ojima I.
,
Suga S.
, and
Abe R.
, Chem. Lett. , 1980 , 853 .
2.
Hatanaka N.
, and
Ojima I.
, Chem. Lett. , 1981 , 231 .
3.
Yoshioka T.
,
Tsuchida T.
,
Tone H.
, and
Okamoto R.
, Eur. Patt. Appl. , 10. 04. 1991 , EP 0 421 440 A2.
4.
Banik B. K.
,
Barakat K. J.
,
Wagle D. R.
,
Manhas M. S.
, and
Bose A. K.
J. Org. Chem. , 1999 , 64 , 5746 .
5.
Gunda G.
, and
Durst T.
J. Org. Chem. , 1983 , 48 , 2092 .
6.
Simig Gy.
,
Fetter J.
,
Hornyák Gy.
,
Zauer K.
, and
Doleschall G.
, Acta Chim. Hung. , 1985 , 119 , 1 , 17.
7.
Tombor Z.
,
Greff Z.
,
Nyitrai J.
, and
Kajtár-Peredy M.
, Liebigs Ann. Org. Bioorg. Chem , 1995 , 5 , 825 .
8.
Hignett K.
, J. Soc. Chem. Ind. London , 1935 , 54 , 98 .
9.
Fritz H.
,
Lehmann J.
, and
Schlesselmann P.
, Carbohydr. Res. , 1983 , 113 , 71 .
10.
Fetter J.
,
Keskeny E.
,
Czuppon T.
,
Lempert K.
,
Kajtár-Peredy M.
, and
Tamás J.
, J. Chem. Soc. Perkin Trans. 1. , 1992 , 3061 .
11.
Le Thanh G.
,
Fetter J.
,
Lempert K.
,
Kajtár-Peredy M.
, and
Gömöry Á.
, Tetrahedron , 1996 , 52 , 30 , 10169.
12.
Palomo C.
,
Ontoria J. M.
,
Odrizola J. M.
,
Alzpurua J. M.
, and
Ganboa I.
, J. Chem. Soc. Chem. Commun. , 1990 , 3 , 248 .
13.
Sápi A.
,
Bertha F.
,
Fetter J.
,
Kajtár-Peredy M.
,
Keserü M. Gy.
, and
Lempert K.
, Tetrahedron , 1996 , 52 , 3 , 771.
14.
Garegg P. J.
, and
Samuelsson B.
, J. Chem. Soc. Chem. Commun. , 1979 , 978 .
15.
Lange G. L.
, and
Gottards C.
, Synth. Commun. , 1990 , 20 , 1473 .
16.
Cooke M. P.
, and
Pollock C. M.
, J. Org. Chem. , 1993 , 58 , 26 , 7474.
17.
Yu M.
,
Zhang Y.
, and
Qian C.
, J. Chem. Res. Synop. , 1998 , 5 , 256 .
18.
Kano S.
,
Ebata T.
, and
Shibuya S.
, J. Chem. Soc. Perkin Trans. 1. , 1980 , 2105 .
19.
Kawabata T.
,
Minami T.
, and
Hiyama T.
, J. Org. Chem. , 1992 , 57 , 6 , 1864.
20.
Desmukh A. R.
,
Zhang H.
,
duc Tran L.
, and
Biehl E.
, J. Org. Chem. , 1992 , 57 , 8 , 2485.
21.
Le Thanh G.
,
Fetter J.
,
Kajtár-Peredy M.
,
Lempert K.
, and
Bertha F.
, Tetrahedron , 1999 , 55 , 8457 .