Synthesis of N6-phosphorylated sydnone imines and their functionalization via 4-Li derivatives. Novel bicyclic sydnone imines

The highly efficient gram-scale method for preparation of up to date hardly available N6-phosphorylated sydnone imines based on the reaction of sydnone imine hydrochlorides with substituted phosphinate or phosphonate acids chlorides in the presence of a base was elaborated. A possibility of straight...

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Published inTetrahedron Vol. 74; no. 22; pp. 2693 - 2702
Main Authors Samarskaya, Alina S., Cherepanov, Ilya A., Godovikov, Ivan A., Dmitrienko, Artem O., Moiseev, Sergey K., Kalinin, Valery N., Hey-Hawkins, Evamarie
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 31.05.2018
Subjects
Bicyclic sydnone imines
Li-derivatives
Mesoionic heterocyclic
Phosphorylated derivatives
Sydnone imine
Li-derivatives
Mesoionic heterocyclic
Phosphorylated derivatives
Sydnone imine
Bicyclic sydnone imines
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Summary:The highly efficient gram-scale method for preparation of up to date hardly available N6-phosphorylated sydnone imines based on the reaction of sydnone imine hydrochlorides with substituted phosphinate or phosphonate acids chlorides in the presence of a base was elaborated. A possibility of straight deprotonation of sydnone imines with n-BuLi followed by the reaction 4-Li-derivatives thus obtained with electrophiles was demonstrated. Novel representatives of bicyclic sydnone imines fused via 4,5-edge of the oxadiazolium ring were obtained. Also sydnone imines containing both phosphorus and sulfur functionalities were obtained with high yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.04.015