1-(Methyl-p-tolyl-amino)-3-phenoxy-2-azetidinones 4-COX and 4-R substituted (COX: X=Me, Et, Ph, NMe2, NEt2, OBut; R=Me, Et, Ph) were smoothly prepared from the corresponding alpha-(methyl-p-tolyl)hydrazonylated ketones, amides and esters via [2+2] cycloaddition with phenoxyketene. The reaction was generally high-yielding and diastereoselective, leading to beta-lactams with a cis relationship between the PhO and the COX moieties, except for R=Ph, where an opposite stereoselectivity was instead observed. The azetidinones represent interesting intermediates which couple protection at N(1) and functionalization at position 4 of the ring. Deprotection of N(1) can be easily attained by oxidative N–N cleavage with magnesium monoperoxyphthalate.

alpha-Oxohydrazones as Imine Component in the Synthesis of 4-Functionalized Azetidinones by the Staudinger Reaction

BIANCHI, LARA;DELL'ERBA, CARLO;MACCAGNO, MASSIMO;MUGNOLI, ANGELO;NOVI, MARINO;PETRILLO, GIOVANNI;SANCASSAN, FERNANDO;TAVANI, CINZIA
2003

Abstract

1-(Methyl-p-tolyl-amino)-3-phenoxy-2-azetidinones 4-COX and 4-R substituted (COX: X=Me, Et, Ph, NMe2, NEt2, OBut; R=Me, Et, Ph) were smoothly prepared from the corresponding alpha-(methyl-p-tolyl)hydrazonylated ketones, amides and esters via [2+2] cycloaddition with phenoxyketene. The reaction was generally high-yielding and diastereoselective, leading to beta-lactams with a cis relationship between the PhO and the COX moieties, except for R=Ph, where an opposite stereoselectivity was instead observed. The azetidinones represent interesting intermediates which couple protection at N(1) and functionalization at position 4 of the ring. Deprotection of N(1) can be easily attained by oxidative N–N cleavage with magnesium monoperoxyphthalate.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11567/246368
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