Abstract |
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.
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Authors | Cornelius J O' Connor, Mark D Roydhouse, Anna M Przybył, Michael D Wall, J Mike Southern |
Journal | The Journal of organic chemistry
(J Org Chem)
Vol. 75
Issue 8
Pg. 2534-8
(Apr 16 2010)
ISSN: 1520-6904 [Electronic] United States |
PMID | 20302382
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Alkenes
- Nitro Compounds
- Thiophenes
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Topics |
- Alkenes
(chemistry)
- Nitro Compounds
(chemistry)
- Thiophenes
(chemical synthesis, chemistry)
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