Chemistry of Heterocyclic Compounds

, volume 44 , issue 5 , pages 576-584

Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes

A P Kadina ¹

M.S. Novikov ¹

A F Khlebnikov ¹

J Magull ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Chemistry Faculty, St. Petersburg State University, St. Petersburg, Russia |

Inorganic Chemistry Institute, Georg-August University, Göttingen, Göttingen, Germany |

Publication type: Journal Article

Publication date: 2008-05-01

Springer Nature

Chemistry of Heterocyclic Compounds

scimago Q4

wos Q4

SJR: 0.243

CiteScore: 2.7

Impact factor: 1.0

ISSN: 00093122, 15738353

DOI: 10.1007/s10593-008-0077-6

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Organic Chemistry

Abstract

The reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbene to give (1RS,5SR,6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes has been studied. Quantum-chemical calculations using the DFT B3LYP/6-31G(d) method have confirmed that the mechanism of the reaction includes the formation of azirino[c]imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation.

Found

6 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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Kadina A. P. et al. Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes // Chemistry of Heterocyclic Compounds. 2008. Vol. 44. No. 5. pp. 576-584.

GOST all authors (up to 50) Copy

Kadina A. P., Novikov M., Khlebnikov A. F., Magull J. Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes // Chemistry of Heterocyclic Compounds. 2008. Vol. 44. No. 5. pp. 576-584.

RIS |

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TY - JOUR

DO - 10.1007/s10593-008-0077-6

UR - https://doi.org/10.1007/s10593-008-0077-6

TI - Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes

T2 - Chemistry of Heterocyclic Compounds

AU - Kadina, A P

AU - Novikov, M.S.

AU - Khlebnikov, A F

AU - Magull, J

PY - 2008

DA - 2008/05/01

PB - Springer Nature

SP - 576-584

IS - 5

VL - 44

SN - 0009-3122

SN - 1573-8353

ER -

BibTex |

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@article{2008_Kadina,

author = {A P Kadina and M.S. Novikov and A F Khlebnikov and J Magull},

title = {Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes},

journal = {Chemistry of Heterocyclic Compounds},

year = {2008},

volume = {44},

publisher = {Springer Nature},

month = {may},

url = {https://doi.org/10.1007/s10593-008-0077-6},

number = {5},

pages = {576--584},

doi = {10.1007/s10593-008-0077-6}

}

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Kadina, A. P., et al. “Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes.” Chemistry of Heterocyclic Compounds, vol. 44, no. 5, May. 2008, pp. 576-584. https://doi.org/10.1007/s10593-008-0077-6.