Facile synthesis of 3-nitro-2-substituted thiophenes.

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.

• 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)

Chemical References

• Alkenes
• Nitro Compounds
• Thiophenes

Topics

• Alkenes (chemistry)
• Nitro Compounds (chemistry)
• Thiophenes (chemical synthesis, chemistry)