Abstract
Stereocontrolled synthesis of 3-vinyl-2-azetidinones has been achieved by the condensation of imines and conjugated acids using phosphorus oxychloride. Transformation of these compounds to other useful intermediates has also been accomplished. Some of the compounds possess antimicrobial activity against both gram positive and gram negative bacteria.
Keywords
References
1.
Bose A.K.
,
Spiegelman G.
, and
Manhas M. S.
, Tetrahedron Lett. , 1971 , 34 , 3167 .
2.
Manhas M.S.
,
Banik B. K.
,
Mathur A.
,
Vincent J. E.
, and
Bose A. K.
, Tetrahedron , 2000 , 56 , 5587 .
3.
Manhas M.S.
,
Ghosh M.
, and
Bose A. K.
, J. Org. Chem. , 1990 , 55 , 575 .
4.
For recent reviews, see: (a)
Thomas R.C.
, Recent Progress in the Chemical Synthesis of Antibiotics , Springer-Verlag , Berlin , 1990 , 533 .
5.
Palomo C.
, in Recent Progress in the Chemical Synthesis of Antibiotics , Springer-Verlag , Berlin , 1990 , 565 .
6.
Perrone E.
, and
Franceschi G.
, Recent Progress in the Chemical Synthesis of Antibiotics , Springer-Verlag , Berlin , 1990 , 613 .
7.
Bose A.K.
,
Krishnan L.
,
Wagle D. R.
, and
Manhas M. S.
, Tetrahedron Lett. , 1986 , 27 , 5955 .
8.
Zamboni R.
, and
Just G.
, Can. J. Chem. , 1979 , 57 , 1945 .
9.
Georg G.I.
,
Mashava P. M.
, and
Guan X.
, Tetrahedron Lett. , 1991 , 32 , 581 .
10.
Mukaiyama T.
, Angew. Chem. Int. Educ. Engl. , 1979 , 18 , 707 .
11.
Torii S.
,
Okumoto H.
,
Sadakane M.
,
Abdul Hai A. K. M.
, and
Tanaka H.
, Tetrahedron Lett. , 1993 , 34 , 6553 .
12.
Guttman V.J.
, J. Inorg. Chem. , 1961 , 582 .
13.
Sharma S.D.
, and
Kanwar S.
, Ind. J. Chem. , 1998 , 965 .
14.
Sharma S.D.
, and
Gupta P. K.
, Tetrahedron Lett. , 1978 , 4587 .
15.
Sharma S.D.
,
Anand R. D.
, and
Kaur G.
, Synth. Commun. , 2004 , 10 , 1855 .
16.
O'Leary A.C.
,
Waldron C. M.
,
Burke C. M.
,
Keaveny R. D.
, and
Meegan M. J.
, J. Chem. Res. (S), 1998 , 64 ; (M) 434.
17.
Meegan M.J.
,
Waldron C. M.
,
Keaveny R. D.
, and
Neary A. D.
, J. Chem. Res. (S), 1997 , 158 ; (M) 1101.
18.
O'Leary A.C.
,
Neary A. D.
,
Waldron C. M.
, and
Meegan M. J.
, J. Chem. Res. (S), 1996 , 368 ; (M) 2162.
19.
Kronenthal D.R.
,
Han C. Y.
, and
Taylor M. K.
, J. Org. Chem. , 1982 , 47 , 2765 .
20.
Bose A.K.
,
Manhas M. S.
,
Ghosh M.
,
Shah M.
,
Raju V. S.
,
Bari S. S.
,
Newaz S. N.
,
Banik B. K.
,
Chaudhary A. G.
, and
Barakat K. J.
, J. Org. Chem. , 1991 , 56 , 6968 .
21.
Janssen C.G. M.
,
Simons L. H. J. G.
, and
Godefroi E. F.
, Synthesis , 1982 , 389 .
22.
Belluci G.
,
Chiappe C.
, and
Moro G. L.
, J. Org. Chem. , 1995 , 60 , 6214 .
23.
Bose A.K.
,
Banik B. K.
,
Newaz S. N.
, and
Manhas M. S.
, Synlett , 1993 , 897 .