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Synthesis 2010(10): 1736-1740  
DOI: 10.1055/s-0029-1218713
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of [1-(Dimethylamino)alkyl]phosphonates from (1-Hydroxy­alkyl)phosphonates: Transformation of Allylic Hydroxyphosphonates into Allylic Aminophosphonates

Babak Kaboudin*, Mohammad Reza Faghihi
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 10 February 2010
Publication Date:
26 March 2010 (online)

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Abstract

A noncatalyzed reaction of (1-hydroxyalkyl)phosphonates with N,N-dimethylformamide diethyl acetal for the synthesis of novel [1-(dimethylamino)alkyl]phosphonates is described. Treatment of allylic (1-hydroxyalkyl)phosphonates with N,N-di­methylformamide diethyl acetal without any catalyst and under reflux in xylene gives novel allylic [1-(dimethylamino)alkyl]phosphonates. By using this method, a series of [1-(dimethylamino)alkyl]phosphonates was synthesized in good yields.

Key words

1-aminophosphonates - 1-hydroxyphosphonates - N,N-dimethylformamide diethyl acetal - allylic alcohols - allylic amines

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