AZIRINO[<i>c</i>]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 (1<i>RS</i>,5<i>SR</i>,6<i>RS</i>)-4-(ALK-1-ENYL)-1,5-DIARYL-3,7,7-TRICHLORO-2,4-DIAZA-BICYCLO[4.1.0]HEPT-2-ENES

Authors

  • А. П. Кадина Chemistry Faculty, St. Petersburg State University, St. Petersburg 198504
  • М. С. Новиков Chemistry Faculty, St. Petersburg State University, St. Petersburg 198504
  • А. Ф. Хлебников Chemistry Faculty, St. Petersburg State University, St. Petersburg 198504
  • Й. Магулл Inorganic Chemistry Institute, Georg-August University, Göttingen, D-37077 Göttingen

DOI:

https://doi.org/10.1007/7057

Keywords:

aziridines, carbenes, imidazoles, iminium ylides, pyrimidines, cascade reactions, domino reactions.

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.

How to Cite
Kadina, A. P.; Novikov, M. S.; Khlebnikov, A. F.; Magull, J.  Chem. Heterocycl. Compd. 2008, 44, 576. [Khim. Geterotsikl. Soedin. 2008, 730.]

For this article in the English edition see DOI 10.1007/s10593-008-0077-6


Downloads

Published

2022-09-15

Issue

No. 5 (2008)

Section

Original Papers