| Autor: |
O' Connor CJ; Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland., Roydhouse MD, Przybył AM, Wall MD, Southern JM |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2010 Apr 16; Vol. 75 (8), pp. 2534-8. |
| DOI: |
10.1021/jo902656y |
| Abstrakt: |
A new approach to 3-nitro-2-substituted thiophenes has been developed. Exposure of commercially available 1,4-dithane-2,5-diol to nitroalkenes in the presence of 20% triethylamine results in a tandem Michael-intramolecular Henry reaction to form the corresponding tetrahydrothiophene. Subsequent microwave irradiation on acidic alumina in the presence of chloranil effects the solvent free dehydration and aromatization to form 3-nitro-2-substituted thiophenes cleanly and rapidly. A simple workup procedure removes the requirement for purification by chromatography in most cases. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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