Preparation of new nitrogen-bridged heterocycles. 51. Syntheses and structures of compounds having two indolizine nuclei in a molecule.
New compounds having two indolizine nuclei in a molecule were prepared in low to moderate yields from the reactions of potassium 2-indolizinethiolates with 1,omega-dihalides such as 1,2-diiodoethane, 1,3-dibromopropane, 1,4-dibromobutane, alpha,alpha'-dichloro-o-xylene, and alpha,alpha'-dichloro-p-xylene. Most of the products had the conformation in which the two indolizine rings in the molecule are as remote as possible, but only 1,2-bis[[(2-indolizinyl)thio]methyl]benzene derivatives, prepared from potassium 2-indolizinethiolates and alpha,alpha'-dichloro-o-xylene, showed a weak attractive interaction between the two indolizine nuclei in the X-ray analysis and the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum.
Kakehi
A
A
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano, Japan. akakehi@gipwc.shinshu-u.ac.jp
Ito
S
S
Suga
H
H
Sakurai
S
S
Kobayashi
T
T
D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D006572:Heterocyclic Compounds, Bridged-Ring; D007212:Indolizines; D017672:Nitrogen Compounds; C035094:indolizine