Reactions of N-hydroxysuccinimide esters of N-alkoxycarbonyl-α-amino acids with active methylene compounds. Synthesis of 3-substituted tetramic acids
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 11,p. 1323-1324
- https://doi.org/10.1039/cc9960001323
Abstract
The N-hydroxysuccinimide esters of N-alkoxycarbonyl-α-amino acids react with active methylene compounds (cyanoacetic esters, malonic and acyl acetic esters), under basic conditions, to produce 3-substituted N-alkoxycarbonyl tetramic acids; in the case of the N-hydroxysuccinimide esters derived from L-aminoacids, the corresponding optically active tetramic acids are obtained.Keywords
This publication has 17 references indexed in Scilit:
- A cycloaddition approach to 3-acyltetramic and 3-acyltetronic acidsJournal of the Chemical Society, Perkin Transactions 1, 1994
- Further reactions of t-butyl 3-oxobutanthioate and t-butyl 4-diethyl-phosphono-3-oxobutanthioate : Carbonyl coupling reactions, amination, use in the preparation of 3-acyltetramic acids and application to the total synthesis of fuligorubin A.Tetrahedron, 1992
- A new pyrone strategy for the synthesis of 3-acyltetramic acidsTetrahedron Letters, 1989
- A general method for the synthesis of tetramic acid derivativesThe Journal of Organic Chemistry, 1988
- Use of t-butyl 4-diethylphosphono-3-oxobutanethioate for tetramic acid synthesis: Total synthesis of the plasmodial pigment fuligorubin ATetrahedron Letters, 1988
- Acylaminoacetyl derivatives of active methylene compounds. 2. The cyclization of the acetylaminoacetyl derivatives to α‐substituted tetramic acids and the formation of N‐acetyl‐α‐substituted tetramic acidsJournal of Heterocyclic Chemistry, 1985
- Acylaminoacetyl derivatives of active methylene compounds. 1. The cyclization of the benzoylaminoacetyl derivatives to α‐substituted tetramic acidsJournal of Heterocyclic Chemistry, 1982
- Methodology for the synthesis of phosphorus-activated tetramic acids: applications to the synthesis of unsaturated 3-acyltetramic acidsThe Journal of Organic Chemistry, 1982
- Synthesis of pyrrolidine-2,4-diones(tetramic acids) and some derivativesJournal of the Chemical Society, Perkin Transactions 1, 1972
- Derivatives of acetoacetic acid. Part VII. α-Acetyltetramic acidsJournal of the Chemical Society, 1954