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Synthesis of Fused Tertazole- and Imidazole Derivatives via Iodocyclization.

Ek, Fredrik LU ; Wistrand, Lars-Göran and Frejd, Torbjörn LU (2003) In Tetrahedron 59(35). p.6759-6769
Abstract
The possibility to prepare fused tetrazole- and imidazole derivatives by iodocyclization in moderate to excellent yields is demonstrated. In some examples the cyclizations were not following Baldwin's rules entirely, i.e. exo-selectivity. Nucleophilic substitution of the formed iodides gave different results depending on the hardness of the nucleophile. Thus, elimination of the iodide could be a problem but a substitution reaction with ethyl potassium xanthate and a radical reaction using acrylonitrile were tolerated. In addition, we showed that it is possible to selectively use three iodo substituents individually in one of the fused imidazole derivatives.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
59
issue
35
pages
6759 - 6769
publisher
Elsevier
external identifiers
  • wos:000184960000006
  • scopus:0042158496
ISSN
0040-4020
DOI
language
English
LU publication?
yes
id
9e89c8d9-5ad0-401e-8a9b-67cc8e55b5f7 (old id 128558)
date added to LUP
2007-07-10 09:38:22
date last changed
2018-05-29 11:28:09
@article{9e89c8d9-5ad0-401e-8a9b-67cc8e55b5f7,
  abstract     = {The possibility to prepare fused tetrazole- and imidazole derivatives by iodocyclization in moderate to excellent yields is demonstrated. In some examples the cyclizations were not following Baldwin's rules entirely, i.e. exo-selectivity. Nucleophilic substitution of the formed iodides gave different results depending on the hardness of the nucleophile. Thus, elimination of the iodide could be a problem but a substitution reaction with ethyl potassium xanthate and a radical reaction using acrylonitrile were tolerated. In addition, we showed that it is possible to selectively use three iodo substituents individually in one of the fused imidazole derivatives.},
  author       = {Ek, Fredrik and Wistrand, Lars-Göran and Frejd, Torbjörn},
  issn         = {0040-4020},
  language     = {eng},
  number       = {35},
  pages        = {6759--6769},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Synthesis of Fused Tertazole- and Imidazole Derivatives via Iodocyclization.},
  url          = {http://dx.doi.org/},
  volume       = {59},
  year         = {2003},
}