The cyanoborane adduct of diethyl ((dimethylamino)methyl)phosphonate, (Et0)2P(0)CH2NMe2-BH2CN (1), was N-alkylated with Et3OBF4 to give the nitrilium salt (Et0)2P(0)CH2NMe2-BH2CNEtBF4 (2). Hydrolysis of 2 with water gave the corresponding carboxyborane (Et0)2P(0)CH2NMe2-BH2C02H (3), and with alkali gave the carbamoyl derivative (Et0)2P(0)-CH2NMe2-BH2CONHEt (4). Reaction of the carbamoyl compound 4 with Et3OBF4 followed by base treatment resulted in the formation of an imino ether, (Et0)2P(0)CH2NMe2-BH2C(0Et)=NR ( 5), which on hydrolysis yielded the ester (Et0)2P(0)-CH2NMe2-BH2C02Et (6). Compound 6 could be obtained in higher yields by an exchange reaction between the (aminomethyl)phosphonate and 0(CH2CH2)2NCH3-BH2C02Et. The borane adduct (Et0)2P(0)CH2NMe2'BH3 (7) was formed directly by reaction of the (aminomethyl)phosphonate and BHyTHF. These compounds were characterized by spectroscopic methods and elemental analysis.
242ChemInform Abstract Coupling of the alkyl phosphites (I) with the aldehydes (II) and the dialkylamines (III) produces the phosphonates (IV) which form the corresponding salts (V). The derivatives (Vb) show anti-viral activity against Herpes simplex and Influenza A virus.
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