DOI: 10.1039/A702638B
(Paper)
Reference Section for: J. Chem. Res. (S), 1998, 30-31
The Reaction of Ethyl 2-Chloroacetoacetate with 2-(Alkylamino) Alcohols: an Unexpected Formation of the 2-Methyloxazolidine Ring†
(Note: The full text of this document is currently only available in the PDF Version )
Lubomir Nechev, Alexander Dobrev, Ivailo Ivanov and Tzvetanka Cholakova
Abstract
The reaction of 2-(alkylamino) alcohols and ethyl 2-chloroacetoacetate in the presence of sodium alkoxides proceeds with unexpected formation of 2-hydroxy-2-(2-methyloxazolidin-2-yl)acetic esters instead of the aza analogues of carboxin (5,6-dihydro-1,4-oxazines) as previously reported in the literature.
References
- B. von Schmeling and M. Kulka, Science, 1966, 152, 659 CAS
.
- B. von Schmeling,
M. Kulka,
D. S. Thiara and
W. A. Harrison,
U.S. Pat., 3249499,
1966(Chem. Abstr.,
1966,
65,
7190g) Search PubMed
- M. Kulka, Can. J. Chem., 1980, 58, 2044 CAS
- B. von Schmeling,
M. Kulka,
D. S. Thiara and
W. A. Harrison,
U.S. Pat., 3393202,
1968(Chem. Abstr.,
1967,
66,
95055w) Search PubMed
- M. Baues, V. Kraatz and F. Korte, Liebigs Ann. Chem., 1973, 1310 Search PubMed
- N. Cromwell and K. Tsuo, J. Am. Chem. Soc., 1949, 71, 993 CAS
- J. Lutz, J. Freek and R. Murphy, J. Am. Chem. Soc., 1972, 94, 8722 CrossRef
- S. Yakimovich and V. Nikolaev, Zh. Org. Khim., 1981, 17, 1104
- R. Lutz and R. Jordan, J. Am. Chem. Soc., 1949, 71, 996 CAS
- Ph. Weintkaub, D. Meyer and Ch. Aiman, J. Org. Chem., 1980, 45, 4989 CrossRef
- S. Yakimovich and V. Nikolaev, Zh. Org. Khim., 1982, 18, 1173 CAS
- P. Vainiotalo, P. Savilainen, M. Ahlgrien, P. J. Malkonen and J. Vepsalainen, J. Chem. Soc., Perkin Trans. 2, 1991, 735 RSC