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

Samarskaya A.S., Cherepanov I.A., Godovikov I.A., Dmitrienko A.O., Moiseev S.K., Kalinin V.N., Hey-Hawkins E.
Тип документаJournal Article
Дата публикации2018-05-31
Название журналаTetrahedron
ИздательElsevier
КвартильQ2
ISSN00404020, 14645416
  • Organic Chemistry
  • Drug Discovery
  • Biochemistry
Краткое описание
Abstract 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.
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1. Samarskaya A.S. и др. Synthesis of N-phosphorylated sydnone imines and their functionalization via 4-Li derivatives. Novel bicyclic sydnone imines // Tetrahedron. 2018. Т. 74. № 22. С. 2693–2702.
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TY - JOUR

DO - 10.1016/j.tet.2018.04.015

UR - http://dx.doi.org/10.1016/j.tet.2018.04.015

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

T2 - Tetrahedron

AU - Samarskaya, Alina S.

AU - Cherepanov, Ilya A.

AU - Godovikov, Ivan A.

AU - Dmitrienko, Artem O.

AU - Moiseev, Sergey K.

AU - Kalinin, Valery N.

AU - Hey-Hawkins, Evamarie

PY - 2018

DA - 2018/05

PB - Elsevier BV

SP - 2693-2702

IS - 22

VL - 74

SN - 0040-4020

ER -

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@article{2018,

doi = {10.1016/j.tet.2018.04.015},

url = {https://doi.org/10.1016%2Fj.tet.2018.04.015},

year = 2018,

month = {may},

publisher = {Elsevier {BV}},

volume = {74},

number = {22},

pages = {2693--2702},

author = {Alina S. Samarskaya and Ilya A. Cherepanov and Ivan A. Godovikov and Artem O. Dmitrienko and Sergey K. Moiseev and Valery N. Kalinin and Evamarie Hey-Hawkins},

title = {Synthesis of N-phosphorylated sydnone imines and their functionalization via 4-Li derivatives. Novel bicyclic sydnone imines}

}

MLA
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Samarskaya, Alina S. et al. “Synthesis of N-Phosphorylated Sydnone Imines and Their Functionalization via 4-Li Derivatives. Novel Bicyclic Sydnone Imines.” Tetrahedron 74.22 (2018): 2693–2702. Crossref. Web.