Synthesis of 1,3,6-Trisubstituted Azulenes

Leino, Teppo Olavi; Baumann, Marcus; Yli-Kauhaluoma, Jari; Baxendale, Ian R.; Wallén, Erik Aarne Anders

Abstract

We have developed a short, general synthetic route to 1,3,6-trisubstituted azulenes. The key intermediate, 6-methylazulene, was synthesized from readily available and inexpensive starting materials in 63% yield over two steps. The methyl group of 6-methylazulene was then used as a synthetic handle to introduce different substituents at the 6-position via two different methods. Subsequently, the 1- and 3-positions were substituted with additional functional handles, such as formyl, chloromethylketone, and iodide. The efficiency of the synthetic route was demonstrated by preparing a collection of three different products with the best demonstrated yield 33% over seven steps.

Citation

Leino, T. O., Baumann, M., Yli-Kauhaluoma, J., Baxendale, I. R., & Wallén, E. A. A. (2015). Synthesis of 1,3,6-Trisubstituted Azulenes. Journal of Organic Chemistry, 80(22), https://doi.org/10.1021/acs.joc.5b02271

• Journal Article Type: Article
• Acceptance Date: Nov 3, 2015
• Publication Date: 2015-11
• Deposit Date: Nov 11, 2015
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 80
• Issue: 22
• DOI: https://doi.org/10.1021/acs.joc.5b02271
• Public URL: https://durham-repository.worktribe.com/output/1426928