THE SYNTHESIS OF α-(4-ANTIPYRYL)AMINO-(SUBSTITUTED) PHENYL-METHYLPHOSPHONIC ACID DERIVATIVES

α-(4-antipyryl)amino-(substituted)phenylmethylphosphonic acid diesters (2) were synthesized by the addition of phosphite diesters to corresponding imine (1). A five-member cyclic transition state was proposed, and the influence of substituents on the reactivity of substrate was discussed. The net at...

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Published inPhosphorus, sulfur, and silicon and the related elements Vol. 155; no. 1; pp. 137 - 145
Main Authors Li, Zai-Guo, Huang, Run-Qiu, Shao, Rui-Lian, Zhao, Yang, Long, Yun-Xian
Format Journal Article
LanguageEnglish
Published ABINGDON Taylor & Francis Group 01.12.1999
Taylor & Francis
Subjects
4-aminoantipyrine
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
imine
phosphite diester
Physical Sciences
Science & Technology
α-aminophosphonic acid: trimethyl silylition: net atomic charge
net atomic charge
trimethyl silylition
alpha-aminophosphonic acid
4-aminoantipyrine
phosphite diester
imine
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Summary:α-(4-antipyryl)amino-(substituted)phenylmethylphosphonic acid diesters (2) were synthesized by the addition of phosphite diesters to corresponding imine (1). A five-member cyclic transition state was proposed, and the influence of substituents on the reactivity of substrate was discussed. The net atomic charges of some imine 1 was calculated to support the mechanism. In the presence of NaI or KI, the cleavage of methyl esters of 2a and 2c vere realized by trimethyl silylition of 2 with trimethylchlorosilane. The structures of the compounds were confirmed by 1 H NMR spectroscopy.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509908044977