Phosphonates and bisphosphonates are stable analogs of phosphates and pyrophosphates that are characterized by one and two carbon–phosphorus bonds, respectively. Among the various phosphonates and bisphosphonates, hydroxy and amino substitutes are of interest as effective in medicinal and industrial chemistry. For example, hydroxy bisphosphonates have proven to be effective for the prevention of bone loss, especially in osteoporotic disease. On the other hand, different substitutions on the carbon atom connected to phosphorus have led to the synthesis of many different hydroxy- and amino-phosphonates and -bisphosphonates, each with its distinct physical, chemical, biological, therapeutic, and toxicological characteristics. Dialkyl or aryl esters of phosphonate and bisphosphonate compounds undergo the hydrolysis process readily and gave valuable materials with wide applications in pharmaceutical and agriculture. This review aims to demonstrate the ongoing preparation of various classes of hydroxy- and amino-phosphonates and -bisphosphonates. Furthermore, the current review summarizes and comprehensively describes articles on the biological applications of hydroxyl- and amino-phosphonates and -bisphosphonates from 2015 until today.
1-Aminophosphonates are valuable compounds with wide range applications in biological and industry. Various reaction conditions and catalysts have been reported for the synthesis of 1-aminophosphonates via three components (dialkylphos-phite+aldehyde+amine) or two component reaction (dialkylphos-phite+imine). We report here a solvent-free synthesis of 1-aminophosphonates under very mild reaction condition. Three component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1-aminophosphonate in good to excellent yield under solvent- and catalyst-free condition at ambient temperature. Hydrophosphorylation of imines in the presence of dialkylphosphite under same condition gave also 1-aminophosphonates in good to excellent yield. These results showed that the reaction needs no to any catalyst or solvent for activation. It seems a tautomeric form of dialkylphosphite (as one of the components) catalysed the reaction. The reaction yield decreased using any solvent. In addition, a novel method will be reported for the synthesis of N-deprotected 1-aminophosphonates (analogues of 1-amino acids) from N-PMP 1-aminophosphonate in the presence of TCCA. To understand the activity of the dialkylphosphite under solvent free condition, the DFT calculations have provided insight into the basis of this activity.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.