Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles.
p-Iodophenol and its O-MOM-protected ether can be converted into iodoamines 2. These give cross-conjugated ketones 3 on oxidation with hypervalent iodides in the presence of methanol, and the ketones undergo radical cyclization. Exposure of the products to acid or sequential treatment with a Grignar...
Κύριοι συγγραφείς: | , , , |
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Μορφή: | Journal article |
Γλώσσα: | English |
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2005
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_version_ | 1826293268232536064 |
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author | Fletcher, S Clive, D Peng, J Wingert, D |
author_facet | Fletcher, S Clive, D Peng, J Wingert, D |
author_sort | Fletcher, S |
collection | OXFORD |
description | p-Iodophenol and its O-MOM-protected ether can be converted into iodoamines 2. These give cross-conjugated ketones 3 on oxidation with hypervalent iodides in the presence of methanol, and the ketones undergo radical cyclization. Exposure of the products to acid or sequential treatment with a Grignard reagent and acid effects rearomatization to produce benzo-fused nitrogen heterocycles 4. |
first_indexed | 2024-03-07T03:27:29Z |
format | Journal article |
id | oxford-uuid:b98f814c-c951-4b6d-8a0d-5c6f45ad0b5d |
institution | University of Oxford |
language | English |
last_indexed | 2024-03-07T03:27:29Z |
publishDate | 2005 |
record_format | dspace |
spelling | oxford-uuid:b98f814c-c951-4b6d-8a0d-5c6f45ad0b5d2022-03-27T05:03:39ZOxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b98f814c-c951-4b6d-8a0d-5c6f45ad0b5dEnglishSymplectic Elements at Oxford2005Fletcher, SClive, DPeng, JWingert, Dp-Iodophenol and its O-MOM-protected ether can be converted into iodoamines 2. These give cross-conjugated ketones 3 on oxidation with hypervalent iodides in the presence of methanol, and the ketones undergo radical cyclization. Exposure of the products to acid or sequential treatment with a Grignard reagent and acid effects rearomatization to produce benzo-fused nitrogen heterocycles 4. |
spellingShingle | Fletcher, S Clive, D Peng, J Wingert, D Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles. |
title | Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles. |
title_full | Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles. |
title_fullStr | Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles. |
title_full_unstemmed | Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles. |
title_short | Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles. |
title_sort | oxidation of p aminophenols and formal radical cyclization onto benzene rings formation of benzo fused nitrogen heterocycles |
work_keys_str_mv | AT fletchers oxidationofpaminophenolsandformalradicalcyclizationontobenzeneringsformationofbenzofusednitrogenheterocycles AT clived oxidationofpaminophenolsandformalradicalcyclizationontobenzeneringsformationofbenzofusednitrogenheterocycles AT pengj oxidationofpaminophenolsandformalradicalcyclizationontobenzeneringsformationofbenzofusednitrogenheterocycles AT wingertd oxidationofpaminophenolsandformalradicalcyclizationontobenzeneringsformationofbenzofusednitrogenheterocycles |