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Synthesis 2010(20): 3504-3508  
DOI: 10.1055/s-0030-1257889
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Novel Class of β-Lactam Derivatives of 1-Aminophosphonates by Staudinger Ketene-Imine [2+2]-Cycloaddition Reaction

Babak Kaboudin*, Mohammad Bagher Afsharinezhad
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan 45137-66731, Iran
Fax: +98(241)4214949; e-Mail: kaboudin@iasbs.ac.ir;
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Publication History

Received 31 May 2010
Publication Date:
22 July 2010 (online)

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Abstract

A novel class of β-lactam derivatives of 1-aminophosphonates was synthesized by Staudinger [2+2] cycloaddition reaction of ketenes with imines derived from 1-aminophosphonates. Treatment of aromatic aldehydes with ammonia and diethyl phosphite followed by a reaction with ketenes, which are generated from the appropriate acid chloride and a tertiary amine, gave a novel class of β-lactam derivatives of 1-aminophosphonates. The major or, in some cases, sole product of the cycloaddition is the cis-β-lactam.

Key words

1-aminophosphonates - β-lactams - ketenes - imines - [2+2]-cycloaddition reaction

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