Abstract
(Chloromethylene)dimethylammonium chloride 1, is a unique reagent that conveniently and efficiently mediates the amide bond formation in β-lactams via cyclodehydration of β-amino acids leading to β-lactam formation. The process involves the formation of a highly reactive activated ester of a β-amino acid which gets cyclised to the corresponding β-lactam in excellent yield. The reaction proceeds smoothly and cleanly as the by-products formed are the water soluble-dimethyl formamide and triethylamine hydrochloride.
Keywords
References
1.
Durckheimer W.
,
Blumbach J.
,
Lattrell R.
, and
Scheunemann K. H.
, Angew. Chem. Int. Ed. Engl. , 1985 , 24 , 180 .
2.
Stezhko T.V.
,
Skachilova S. Y.
, and
Pleshkov M. G.
, Zh. Org. Khim. , 1974 , 10 , 1556 .
3.
George G.I.
, The Organic Chemistry of b-lactams , VCH , New York 1993 . pp. 295 .
4.
Sharma S.D.
, and
Gupta P. K.
, Tetrahedron Lett. , 1978 , 4587 .
5.
Sharma S.D.
, and
Bhaduri S.
, J. Chem. Res. (S) , 2001 , 321 .
6.
Sharma S.D.
,
Anand R. D.
, and
Kaur G.
, Synth. Commun. , 2004 , 34 , 1 .
7.
Campaigne E.
, and
Archer W. L.
, J. Am. Chem. Soc. , 1953 , 75 , 989 .
8.
Treihs W.
,
Neupert H. J.
, and
Hiebsch J.
, Chem. Ber. , 1959 , 92 , 141 .
9.
Procopiou P.A.
,
Brodie A. C.
,
Deal M. J.
, and
Hayman D. F.
, Tetrahedron Lett. , 1993 , 34 , 7483 .
10.
Procopiou P.A.
,
Brodie A. C.
,
Deal M. J.
, and
Hayman D. F.
, J. Chem. Soc. Perkin Trans. 1 , 1996 , 2249 .
11.
Zaoral M.
, and
Arnold Z.
, Tetrahedron Lett. , 1960 , 9 .
12.
Eilingsfeld H.
,
Seefelder M.
, and
Weidinger H.
, Angew Chem. , 1960 , 72 , 836 .
13.
Hepburn D.R.
, and
Hudson H. R.
, J. Chem. Soc., Perkin Trans. 1 , 1976 , 754 .
14.
Barrett A.G. M.
,
Koike N.
, and
Procopiou A.
, J. Chem. Soc. Chem. Commun. , 1995 , 1403 .
15.
Barrett A.G. M.
,
Braddock D. C.
,
James R. A.
, and
Procopiou A.
, J. Chem. Soc. Chem. Commun. , 1997 , 433 .
16.
Blicke F.F.
, and
Gould W. A.
, J. Org. Chem. , 1958 , 23 , 1102 .
17.
Zilkha A.
, and
Rivlin J.
, J. Org. Chem. , 1958 , 23 , 94 .
18.
Johnson T.B.
, and
Lovak J. E.
, J. Am. Chem. Soc. , 1936 , 58 , 299 .
19.
Holley R.W.
, and
Holley A. D.
, J. Am. Chem. Soc. , 1949 , 71 , 2129 .
20.
Holley R.W.
, and
Holley A. D.
, J. Am. Chem. Soc. , 1949 , 71 , 2124 .
