The acidic cleavage of pyridylmethyl(amino)phosphonates. Formation of the corresponding amines
Hydrolysis of 3-pyridylmethyl(amino)phosphonates by means of 20% aq. hydrochloric acid gave corresponding 3-pyridimethyl(amino)phosphonic acids, as expected. However, hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to decomposition of the phosphonates with a cleavage of C-P bond and formation of the corresponding amines. The leaving phosphorus moiety was identified as phosphoric acid. The scope of the reaction is limited to 2- and 4-pyridylmethyl derivatives of aminophosphonic acids and their esters, as well as to the derivatives possessing similar structure. On the contrary, the basic hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to the corresponding monoalkyl esters of the aminophosphonates, and no cleavage of C-P bond was observed in those cases.
Boduszek, Bogdan
p. 12483 - 12494
(2007/10/03)
31. Synthesis of a masked p-quinone methide β-lactam as an active metabolite of nocardicins
Nocardicin A analogues 30, 34, and 38 as well as the highly strained quinone methide 43 were synthesized. β-Lactam 34 was found biologically active against several Gram-negative microorganisms in vitro; pyridinium N-oxide derivative 38 possessed activity
Hakimelahi,Tsay,Hwu
p. 411 - 420
(2007/10/02)
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