, volume 64 , issue 32 , pages 7524-7530

Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines

Ekaterina Yu Shinkevich ¹

Kourosch Abbaspour Tehrani ¹

Alexander F Khlebnikov ²

Mikhail S. Novikov ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Faculty of Sciences, Department of Applied Biological Sciences and Engineering, Laboratory of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium |

Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg,Petrodvorets,Russia |

Publication type: Journal Article

Publication date: 2008-08-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2008.05.121

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

Abstract 3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the C N double bond of β-chloroimines. Under the action of Lewis acids or HCl, N–C 3 bond cleavage occurred, giving rise to N -substituted 2,4-dichloro-3,3-dimethylbutanamides, which were further converted to 3-chloropyrrolidin-2-ones under alkaline conditions. When 2,2-dichloro-3-(2-chloro-1,1-dimethylethyl)-1-phenylaziridine was reacted with sodium methoxide, aziridine ring opening with N–C 2 bond cleavage took place, leading to methyl 4-chloro-3,3-dimethyl-2-(phenylamino)butanoate.

Found

5 citations

Novikov Mikhail

DSc in Chemistry, associate professor

216 publications, 4 151 citations, 54 reviews

h-index: 33

Saint Petersburg State University

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Shinkevich E. Yu. et al. Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines // Tetrahedron. 2008. Vol. 64. No. 32. pp. 7524-7530.

GOST all authors (up to 50) Copy

Shinkevich E. Yu., Abbaspour Tehrani K., Khlebnikov A. F., Novikov M. S. Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines // Tetrahedron. 2008. Vol. 64. No. 32. pp. 7524-7530.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2008.05.121

UR - https://doi.org/10.1016/j.tet.2008.05.121

TI - Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines

T2 - Tetrahedron

AU - Shinkevich, Ekaterina Yu

AU - Abbaspour Tehrani, Kourosch

AU - Khlebnikov, Alexander F

AU - Novikov, Mikhail S.

PY - 2008

DA - 2008/08/01

PB - Elsevier

SP - 7524-7530

IS - 32

VL - 64

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2008_Shinkevich,

author = {Ekaterina Yu Shinkevich and Kourosch Abbaspour Tehrani and Alexander F Khlebnikov and Mikhail S. Novikov},

title = {Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines},

journal = {Tetrahedron},

year = {2008},

volume = {64},

publisher = {Elsevier},

month = {aug},

url = {https://doi.org/10.1016/j.tet.2008.05.121},

number = {32},

pages = {7524--7530},

doi = {10.1016/j.tet.2008.05.121}

}

MLA

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Shinkevich, Ekaterina Yu., et al. “Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines.” Tetrahedron, vol. 64, no. 32, Aug. 2008, pp. 7524-7530. https://doi.org/10.1016/j.tet.2008.05.121.