Abstract
Ammonium metavanadate (NH4VO3) is an inexpensive, efficient and mild catalyst for the synthesis of α-hydroxyphosphonate derivatives by the reaction of various aryl or heteroaryl aldehydes with triethylphosphite at room temperature. This method affords the αhydroxyphosphonates in short reaction times, under solvent-free conditions, and in high yield.
Highlights
Phosphonates functionalized with hydroxy and amino groups have attracted considerable attention for their role in biologically relevant processes[1] and wide range of applications.[2] αHydroxyphosphonates act as an inhibitor of a diverse group of enzymes including Renin,3a FPTase,3b HIV protease3c and EPSP synthase.3d they show antibacterial activity with the quinoline nucleus.[4]
In continuation of our research devoted to phosphorus chemistry[4,33] and interest in the development of novel synthetic methodologies,[34] we report a simple, efficient, and rapid method for the synthesis of α-hydroxyphosphonates catalyzed by ammonium metavanadate (Scheme 1)
In our search for an efficient catalyst and the best experimental reaction conditions in the preparation of α-hydroxyphosphonates, we have determined that the reaction of 2chloroquinoline-3-carbaldehyde 1a with triethyl phosphite 2 under solvent-free conditions at room temperature is the standard model reaction
Summary
Phosphonates functionalized with hydroxy and amino groups have attracted considerable attention for their role in biologically relevant processes[1] and wide range of applications.[2] αHydroxyphosphonates act as an inhibitor of a diverse group of enzymes including Renin,3a FPTase,3b HIV protease3c and EPSP synthase.3d they show antibacterial activity with the quinoline nucleus.[4]. In our search for an efficient catalyst and the best experimental reaction conditions in the preparation of α-hydroxyphosphonates, we have determined that the reaction of 2chloroquinoline-3-carbaldehyde 1a with triethyl phosphite 2 under solvent-free conditions at room temperature is the standard model reaction. The use of p-TSA, sulphamic acid and acidic alumina provided the product in moderate yields 54-71% (Table 1, Entry 4-6). NH4VO3 provided the best results, yielding 94% of product yield within 5 min (Table 1, Entry 7).
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