Facile One-pot Synthesis of A Novel Propargyl-Azulene Hybrid Derivative: Cycloaddition Reaction and Some Spectroscopic Properties

Abstract

Guaiazulene, 1,4-dimethyl-7-isopropylazulene, is one of the non-benzenoid aromatic compounds consisting of fused of the seven- and the five-membered ring. Guaiazulene is an important natural product and having great potential due to its unique optical and electronic properties. In this study, a method for propargyl insertion into the C-4 methyl group of the guaiazulene is developed. A one-pot reaction of the guaiazulene, LDA, and propargyl bromide in THF affords the corresponding a new propargyl-azulene hybrid derivative. Additionally, Diels-Alder cycloaddition reaction between the propargyl-GA and tetraphenylcyclopentadienone was performed, and the cycloadduct was obtained with excellent yield. The structures of new compounds were elucidated on the basis of extensive spectroscopic (IR, NMR, and UV-vis) data analysis. This approach may be potentially useful for the development of the new azulene derivatives.

Keywords

• Azulene
• guaiazulene
• propargylation
• alkynylation
• one-pot synthesis
• Diels-Alder
• cycloaddition

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