AN EFFICIENT SYNTHESIS OF 1-AMINOPHOSPHONIC ACIDS AND ESTERS BEARING HETEROCYCLIC MOIETY
- 1 July 1995
- journal article
- research article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 104 (1-4), 63-70
- https://doi.org/10.1080/10426509508042578
Abstract
New α-aminophosphonic esters and acids derived from furan, thiophene and pyrazole were prepared in high yield, in the reactions of benzylamine, benzhydrylaraine or benzyl carbamate with heterocyclic aldehydes and diethyl or diphenyl phosphonates. The protecting groups at amine (benzyl or benzhydryl) were removed by hydrogenolysis or hydrolysis, respectively. The N-benzyloxycarbonyl (Z-group) was removed by treatment with 45% HBr in acetic acid.Keywords
This publication has 19 references indexed in Scilit:
- Novel amidine-containing peptidyl phosphonates as irreversible inhibitors for blood coagulation and related serine proteasesJournal of Medicinal Chemistry, 1994
- Improved Synthesis of New α-Aminophosphonic Acids by Sonochemical ActivationSynthesis, 1994
- Exploration of N-phosphonoalkyl-, N-phosphonoalkenyl-, and N-(phosphonoalkyl)phenyl-spaced .alpha.-amino acids as competitive N-methyl-D-aspartic acid antagonistsJournal of Medicinal Chemistry, 1992
- BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDSPhosphorus, Sulfur, and Silicon and the Related Elements, 1991
- Inhibition of Escherichia coli glutamine synthetase by .alpha.- and .gamma.-substituted phosphinothricinsBiochemistry, 1990
- Kinetic mechanism of Escherichia coli glutamine synthetaseBiochemistry, 1980
- Synthesis ofO,O-Dialkyl 1-AminoalkanephosphonatesSynthesis, 1980
- Diphenyl 1-AminoalkanephosphonatesSynthesis, 1979
- ADVANTAGES OF USING DI(p-METHYLBENZYL) HYDROGEN PHOSPHITE IN SYNTHESIS OF AMINOPHOSPHONATES FROM ALDIMINESChemistry Letters, 1978
- Chemistry of phosphorous acid: new routes to phosphonic acids and phosphate estersThe Journal of Organic Chemistry, 1978