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Synthesis of 1,3,6-Trisubstituted Azulenes

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

Authors

Teppo Olavi Leino

Marcus Baumann

Jari Yli-Kauhaluoma

Erik Aarne Anders Wallén



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.

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