Synthesis of Fused Tertazole- and Imidazole Derivatives via Iodocyclization.
(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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https://lup.lub.lu.se/record/128558
- author
- Ek, Fredrik LU ; Wistrand, Lars-Göran and Frejd, Torbjörn LU
- organization
- publishing date
- 2003
- 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}}, }