Abstract
Acetonitrile as a solvent, excess of primary amines as general bases, and a reflux condition make the multi-component reactions of (2-cyanoacetyl) carbamate 1, ethyl orthoformate, and primary amines form 5-cyanouracils 4a-c feasibly. Mechanistic studies of the multi-component reaction were carried out by proton NMR spectrometer. Acetonitrile as a solvent makes the reaction of 1 with ethyl orthoformate produce E-ethyl (2-cyano-3-ethoxyacryloyl) carbamate E-2 without a catalyst of acetic anhydride. The reactions of E-2 with primary amines produce the corresponding Z-3a-c as the only stable isomers eventually in CDCl3 or CD3CN. General-base-catalyzed intramolecular cyclizations of Z-3a-c at a reflux condition in CD3CN generated the corresponding 5-cyanouracils 4a-c.
Original language | English |
---|---|
Pages (from-to) | 3399-3404 |
Number of pages | 6 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 14 |
Issue number | 10 |
DOIs | |
Publication status | Published - 2006 May 15 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry