One-pot synthesis of N-chloroacetyl 1-aminoalkyl phosphonates - Precursors of 4-phosphono-β-lactams
4-Phosphono-β-lactams are synthesized via a three-step sequence, including final formation of the C3-C4 bond through a phosphorus-stabilized carbanion. The chlorinated precursors can be synthesized via two different methods: a one-pot N-acylation of an aromatic imine followed by addition of a trialkyl phosphite or phosphonylation of a suitable imine followed by N-acylation in a separate reaction step. The former method was preferred because of the ease of the reaction and the good yields obtained. Georg Thieme Verlag Stuttgart.
Moonen, Kristof,Stevens, Christian V.
p. 3603 - 3612
(2007/10/03)
Synthesis of 4-phosphono-β-lactams via phosphite addition to acyliminium salts
4-Aryl-4-phosphono-β-lactams are prepared by acylation of iminium salts with chloroacetyl chloride followed by phosphite addition and ring closure using sodium hydride as a base. Deacylation of the iminium salt is in competition with the desired addition of phosphites to acyliminium salts, which lowers the yield of the reaction.
Stevens, Christian V.,Vekemans, Wannes,Moonen, Kristof,Rammeloo, Thomas
p. 1619 - 1622
(2007/10/03)
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