An efficient method for the azocino[4,3-b]indole framework of strychnos alkaloids: DFT investigations on the electronic and spectroscopic properties

Nesimi Uludağ, Goncagül Serdaroğlu, Naki Çolak
2019 Zenodo  
Department of Chemistry, Nam k Kemal University, 59030, Tekirdag, Turkey Faculty of Education, Sivas Cumhuriyet University, 58140, Sivas, Turkey Department of Chemistry, Faculty of Sciences and Arts, Hitit University, 19030, Çorum, Turkey E-mail: nuludag@nku.edu.tr, serdagroglu@cumhuriyet.edu.tr Manuscript received online 26 April 2019, revised and accepted 20 July 2019 Tetracyclic 1,5-methanoazocino[4,3-b]indole (2) was achieved via a new synthetic approach for the synthesis of related
more » ... s alkaloids. These products embody the ABCD-ring system associated with the title alkaloids, as well as a one-pot construction of the ABCD ring system using tetrachloro-1,4-benzoquinone and tetrafluoro-1,4-benzoquinone, were involved as key steps. Also, the DFT-based quantum chemical calculations have been performed to evaluate the structural, electronic, and spectroscopic properties of the compound. PES (potential energy surface) scan revealed three stable conformers of the compound. The calculated FT-IR and NMR spectral data were compared with the corresponding observed values for the most stable conformer of the compound. Frontier Molecular Orbital analysis has revealed the chemical reactivity tendency and sites of the compound.
doi:10.5281/zenodo.5643495 fatcat:hqys43vkfbbqdmvvyg3f7spvbi