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

Authors : Musa ERDOĞAN

Pages : 2747-2758

Doi:10.21597/jist.735838

View : 10 | Download : 8

Publication Date : 2020-12-15

Article Type : Research Paper

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