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Synthesis of Amidines Derived from Phosphonates and Phosphane Oxides − Amidine‐Mediated Preparation of Phosphorylated Oxazolines
Author(s) -
Palacios Francisco,
Ochoa de Retana Ana María,
Pagalday Jaione
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390139
Subject(s) - chemistry , amidine , acylation , alkylation , bromide , benzoyl chloride , iodide , ethyl chloroformate , methyl iodide , chloride , medicinal chemistry , chloroformate , organic chemistry , catalysis
Alkylation of N ‐(phosphorylalkyl)phosphazenes 2 with methyl iodide and allyl bromide and acylation with ethyl chloroformate leads to the formation of aminophosphonium salts 4 derived from (aminoalkyl)phosphonates. N ‐(Phosphorylalkyl)amidines 8 were obtained by reaction of phosphazenes derived from aminophosphonates with benzoyl chloride and subsequent addition of amines. These functionalized amidines were used as key intermediates in the synthesis of oxazolin‐4‐ylphosphonates 9 and 10 . In a similar manner, oxazolin‐4‐ylphosphane oxides 17 and 18 were prepared from N ‐(phosphanylalkyl)amidines 16 , which were obtained by reaction of phosphazenes derived from phosphane oxides 15 with benzoyl chloride and amines. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)