An effective catalyst-free microwave-assisted synthesis of α-aminophosphonates from ketones in a three-component system was shown. The method affords α-aminophosphonates in high yields from various ketones including natural porphyrine derivatives.
The first synthesis of α-amino phosphonates comprising porphyrin core was accomplished. Three methods of obtaining α-amino phosphonates 5-8 were compared. Conventional heating of formylporphyrins 1-4 with t-BuNH2 and (EtO)2P(O)H in various solvents was ultimately unsuccessful for preparing 5-8 whereas the use of microwave irradiation made it possible to obtain 5-8 in good yields. Regioselective preparation of 5-8 in excellent yields was achieved by combining microwave-assisting conditions and catalysis with CdI2. Efficient synthetic procedures of obtaining formylporphyrins 3,4 in large scale were also proposed.
1 August 2009 in Russian Journal of Organic Chemistry
Reactions of carbonyl compounds of aliphatic, aromatic, and heteroaromatic series with dialkyl phosphites in the presence of DBN were studied under microwave irradiation.
1 October 2010 in Russian Journal of Organic Chemistry
A preparative synthesis was developed for phosphonamino acids esters proceeding from natural amino acids with the use of microwave assistance. A series of phosphonamino acids esters was prepared from optically active natural α-amino acids.