The origin of a common compound about 2689-65-8

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Infrared spectroscopic study of the condensation reaction of halofurfural with ketones, published in 1965, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, Application of 2689-65-8.

The reactions of furfuryl iodide (I) and bromide (II) with ketones were investigated. NaOH (3-5 ml., 5%), 0.05 mole halofurfural, and 0.8-3 ml. ketone were added to 20 ml. solvent. The reaction lasted 1-2 hrs. The product was precipitated with 30-50 ml. H2O and dried. The light-yellow oily products were investigated in C2H4Cl2 solutions, the crystalline products in pressed KBr disks. The compositions of the condensation products of I with methyl nonyl ketone, methyl naphthyl ketone, and acetophenone were C16H23O2I, C17H11O2I, and C13H9O2I, resp. The condensations of II with methyl alkyl ketones, where the alkyl group was Et, Pr, Bu, amyl, hexyl, isopropyl, and isobutyl, and with acetophenone and acetylacetone, led to C9H9O2Br, C10H11O2Br, C11H13O2Br, C12H15O2Br, C13H17O2Br, C10H11O2Br, C11H13O2Br, C13H9O2Br, and C10H9O3Br, resp. The ir spectra indicate the functional groups present in the various products.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem