One‐Pot Synthesis of α‐Aminophosphonates: An Inexpensive Approach.

Abstract

Organo-phosphorus compoundsOrgano-phosphorus compounds S 0080 One-Pot Synthesis of α-Aminophosphonates: An Inexpensive Approach. -A one-pot synthesis of α-aminophosphonates from aldehydes, amines and trimethyl phosphite catalyzed by aluminium chloride at ambient temperature is reported. Slightly better yields are obtained with ZrCl4 instead of AlCl3. -(MANJULA, A.; RAO*, B. V.; NEELAKANTAN, P.; Synth.

Ultrasound-promoted solvent-free synthesis of some new α-aminophosphonates as potential antioxidants

“…They are discovered to be antibacterial (Subramanyam et al, 2017), antifungal (Yang et al, 2006), antiviral (Xu et al, 2006), anti-inflammatory agents (Sujatha et al, 2017), anti-HIV (Bhattacharya et al, 2012), anticancer (Bahrami et al, 2016), anti-proliferative and apoptosis inducing (Huang et al, 2016a(Huang et al, , 2016bLi et al, 2015), antitumor (Liu et al, 2017), herbicidal activity (Che et al, 2016) and insecticidal activity (Jiang et al, 2013;Liu et al, 2012). Addition of trialkyl or dialkylphosphite to imines is a successful technique to obtain them (Azizi et al, 2004;Heydari et al, 2009;Kassaee et al, 2009;Manjula et al, 2013;Yadav et al, 2001). Many reviews were published using various Bronsted acids, Lewis acids, hetero poly acids, heterogeneous and nano catalysts to accomplish this transformation (Ambica et al, 2008;Anastas and Eghbali, 2010;Bhattacharya et al, 2007Bhattacharya et al, , 2008Chandrasekhar et al, 2001;Heydari et al, 2007;Mitragotri et al, 2008;Sobhani et al, 2008;Yadav et al, 2003;Vahdat et al, 2008).…”

Synthesis of α-Amino Phosphonates under a Neat Condition Catalyzed by Multiple-Acidic Ionic Liquids

“…α-Amino phosphonates are an important class of compounds widely used in biochemical and pharmaceutical chemistry due to their structural analogy to α-amino acids and transition state mimics of peptide hydrolysis . Three-component synthesis starting from aldehydes, amines, and diethyl phosphite or triethyl phosphite have been reported catalyzed by Lewis and Bronsted acid, such as HCl or H 2 SO 4 , AlCl 3 , InCl 3 , BF 3 ·Et 2 O, LiClO 4 , SbCl 3 /Al 2 O 3 , sulfamic acid, H 3 BO 3 , FeCl 3 and CuCl 2 , tartaric acid, and other methods . However, many of these methods suffer from some drawbacks such as long reaction times, low yields of the products, requiring stoichiometric amounts of catalysts, use of toxic solvents, and high cost.…”

Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety

“…Another interesting class of compounds called -aminophosphonates which are essentially structural analogues to natural amino acids, exhibit diverse biological activities such as plant virucidal, plant growth regulatory, herbicidal, fungicidal and antitumor effects [15][16][17]. In view of different biological and chemical applications of these compounds, development of suitable synthetic methodologies for their preparation in pure form has been a topic of great interest in the past few decades [18][19][20][21][22]. In order to incorporate the two aforementioned active pharmacophores in a single molecule, we prepared a series of chiral monothiourea derivatives containing an -aminophosphonate moiety by the addition of O,O′-dialkylisothiocyanato(phenyl) methylphosphonate to a chiral amine.…”