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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
; and
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
10.1016/S0040-4020(03)00818-4
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Chemical Biology and Drug Discovery (013210700)
id
9e89c8d9-5ad0-401e-8a9b-67cc8e55b5f7 (old id 128558)
date added to LUP
2016-04-01 15:48:33
date last changed
2022-03-07 01:29:38
@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/10.1016/S0040-4020(03)00818-4}},
  doi          = {{10.1016/S0040-4020(03)00818-4}},
  volume       = {{59}},
  year         = {{2003}},
}