One-Pot Synthesis of α-Aminophosphonates: An Inexpensive Approach

Abstract

A one-pot synthesis of the a-aminophosphonates from aldehydes and amines using trimethyl phosphite catalyzed by aluminum chloride at ambient temperature is reported.

The Kabachnik–Fields Reaction Accelerated in External Magnetic Field

“…All new aminophosphonates 3Ab , 3Ad , and 3Af as well as 3Bb , 3Bd , and 3Bf were characterized by 1 H, 31 P, and 13 C NMR spectroscopy, and their purity was confirmed by elemental analyses. Data of known synthesized aminophsophonates are described in the literature, and their identity was confirmed by 1 H and 31 P NMR spectroscopy, and melting point measurements, which were compared with the literature data . Yields of reactions carried out under influence of magnetic field are also given.…”

“…1 H NMR (CDCl 3 , 600 MHz): δ (ppm) 7.43–7.39 (m, PhH, 2H); 7.36–7.34 (m, PhH, 2H); 7.33–7.31 (m, PhH, 4H); 7.28–7.24 (m, PhH, 2H); 6.62 (ddd, 4 J HH = 1.2 Hz, 4 J PH = 4.8 Hz, 3 J HH = 15.6 Hz, CH = CH, 1H); 6.15 (ddd, 3 J PH = 5.4 Hz, 3 J HH = 6.6 Hz, 3 J HH = 15.6 Hz, CH = CH, 1H); 4.07 (ddd, 4 J HH = 1.2 Hz, 3 J HH = 6.6 Hz, 2 J PH = –25.8 Hz, CHP, 1H); 3.80 (d, 3 J PH = 10.8 Hz, POCH 3 , 3H); 3.79 (d, 2 J HH = –13.2 Hz, CH 2 Ph, 1H); 3.77 (d, 3 J PH = 10.8 Hz, POCH 3 , 3H); 3.76 (d, 2 J HH = −13.2 Hz, CH 2 Ph, 1H). 31 P NMR (CDCl 3 , 243 MHz): δ (ppm) 25.86 .…”

Design and one-pot synthesis of new α-aminophosphonates and antimicrobial activity

“…However, one-pot synthesis of α-aminophosphonates remains a favorite due to its versatile route and high-yielding reactions. Recently, threecomponent synthesis starting from aldehydes, amines and diethylphosphite or triethylphosphite has been reported by using metal chloride catalysts such as InCl 3 , [23] ZrCl 4 , AlCl 3 , [24] SbCl 3 /Al 2 O 3 , [25] and TaCl 5 -SiO 2 . [26] Many of these methods suffer from some drawbacks such as long reaction times, low yields of the products, requiring stoichiometric amounts of catalysts, costly and moisture sensitive catalysts and use of highly toxic or toxic catalysts.…”

Silica gel and polystyrene supported aluminum chloride as heterogeneous catalysts for the preparation of α‐aminophosphonates

“…Three-component condensation of an aldehyde, an amine, and a phosphite is the most convenient method for the preparation of these compounds. Several types of catalysts were introduced previously for this purpose, such as ZrCl 4 [11], AlCl 3 [12], LiClO 4 [13], SiO 2 -NH 4 HCO 3 [14], Al(OTf) 3 [15], ionic liquid [bmim]Cl-AlCl 3 [16], Mg(ClO 4 ) 2 [17], TiCl 4 [18], Al 2 O 3 -SbCl 3 [19], ZrOCl 2 ·8H 2 O [20], TiO 2 [21], amberlyst-15 [22], [Cu(3,4-tmtppa)](MeSO 4 ) 4 [23], sulfamic acid [24], FeCl 3 [25], sodium dodecyl sulfate [26], mesoporous aluminosilicate nanocage [27], and H 3 BO 3 [28]. Most of the above-mentioned methods suffer from the drawbacks such as generation of environmentally perilous waste material, tedious workup, long reaction times, the use of malodorous trialkyl phosphite as the phosphorus nucleophile, unsatisfactory yields, complicated operations, and the use of moisture-sensitive, expensive, hazardous, difficult to handle, or unreusable catalysts.…”