A practical synthesis of α-aminophosphonic acids.

Brain AT1Angiotensin Receptor Subtype Binding: Importance of Peptidase Inhibition for Identification of Angiotensin II as Its Endogenous Ligand

“…Glutamate phosphonate (4-amino-4-phosphonobutyric acid; GluP) was synthesized in house or by Thesis Chemistry (Mentor, OH). In brief, the in-house procedure was as follows: the GluP precursor ester methyl-3-(ethoxyphosphono)-3-aminopropanoate was synthesized in three steps from readily available ethyl-4-chloro-4-oxobutyrate (Kowalik et al, 1981) and subsequently treated with 9 N HCl under reflux for 20 h. The product was precipitated with methanol/propylene oxide (Oleksyszyn and Tyka, 1977) and recrystallized from ethanol, yielding GluP (Genet et al, 1992). Glutamate thiol was a kind gift from Dr. Sherwin Wilk (Mount Sinai School of Medicine, City University of New York, New York, NY).…”

One-Pot Synthesis of 1-Aminophosphinic acids using 50% Hypophosphorus Acid under microwave irradiation

“…All melting points were obtained by 8 Hz, C-P), 108. 2,112.8,114.5,115.9,120.8,129.7,131.7,137.9,147.3 (d,Jc p=13.8 6,57.4 (d,Jc p=99.4 Hz, C-P), 114.…”

“…1-Aminoalkylphosphinic acids, the phosphinic acid analogues of l-amino carboxylic acids, are important compounds that exhibit a variety of interesting and useful properties. In contrast to the widely studied l-aminoalkylphosphonic acid derivatives [5][6][7][8], relatively few papers have been reported on the chemistry of l-aminoalkylphosphinic acids, although there are evidences that a-aminophosphinic acids are pharmacologically active compounds. Formation of l-hydroxyalkylphosphinic acids frequently accompanies the formation of l-aminoalkylphosphinic acids…”

Molecular iodine: An efficient catalyst for the one-pot synthesis of primary 1-aminophosphonates

“…Moreover, aminophosphonates are found as constituents of natural products. There are several multi-step synthetic approaches to primary 1-aminophosphonates in the literature: a) addition of the P-H function to imines and nitriles [5,6], b) Hofmann rearrangement of substituted phosphonoacetic esters [7], c) alkylation of nucleophilic precursors such as Schiff bases [8], d) conversion of the corresponding 1-hydroxyphosphonates to 1-aminophosphonates [9,10] and e) reduction of 1-hydroxy-*Corresponding author. E-mail: ssobhani@birjand.ac.ir primary 1-aminophosphonates: R 3 =H; R 4 =H secondary 1-aminophosphonates: R 3 =alkyl, aryl; R 4 =H tertiary 1-aminophosphonates: R 3 =alkyl, aryl; R 4 =alkyl, aryl NR 3 R 4 P(OR 5 …”