Synthesis of Six and Seven-membered Heterocyclic Molecules Containing an Adamantyl Fragment and an X-ray Crystal Structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl)methanimine

Authors

Shukkur A. Hamed, Department of Chemistry, College of Education for Pure Science, University Of Anbar, Al-Anbar, IraqFollow
Ali S. Ismail, Department of Chemistry, College of Education for Pure Science, University Of Anbar, Al-Anbar, Iraq
Ahmed Dhary Saleh, Department of Chemistry, College of Education for Pure Science, University Of Anbar, Al-Anbar, Iraq

Abstract

Our work included a synthesis of three new imine derivatives—1,3-thiazinan-4-one, 1,3-oxazinan-6-one and 1,3-oxazepin-4,7-dione—which contained an adamantyl fragment. These were produced via the condensation of the Schiff`s base (E)-N-(adamantan-1-yl)-1-(3-aryl)methanimine with 3-mercaptopropanoic acid; 3-chloropropanoic acid; and maleic, citraconic anhydride, respectively. These new imines were prepared via the condensation of adamantan-1-ylamine and 3-nitro-, 3-bromobenzaldehyde in n-BuOH. We obtained a good yield of products. FTIR, 1H NMR spectroscopy and C.H.N.S analysis were used to diagnostic the products. The molecular structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl)methanimine was confirmed by X-ray crystallography analysis.

Keywords

Adamantan-1-ylamine, 1, 3-oxazepin-4, 7-dione, 1, 3-oxazinan-6-one, 1, 3-thiazinan-4-one, X-ray crystallography

Article Type

Supplemental Issue

How to Cite this Article

Hamed, Shukkur A.; Ismail, Ali S.; and Saleh, Ahmed Dhary (2020) "Synthesis of Six and Seven-membered Heterocyclic Molecules Containing an Adamantyl Fragment and an X-ray Crystal Structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl)methanimine," Baghdad Science Journal: Vol. 17: Iss. 1, Article 38.
DOI: https://doi.org/10.21123/bsj.2020.17.1(Suppl.).0272