Synthesis of Amidines Derived from Phosphonates and Phosphane Oxides − Amidine‐Mediated Preparation of Phosphorylated Oxazolines | Zendy

Palacios Francisco | Zendy; Ochoa de Retana Ana María | Zendy; Pagalday Jaione | Zendy

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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)

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