The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Halogen-substituted products of furfural》. Authors are Scheibler, Helmuth; Jeschke, Johannes; Beiser, Willy.The article about the compound:5-Iodo-2-furaldehydecas:2689-65-8,SMILESS:IC1=CC=C(O1)C=O).Reference of 5-Iodo-2-furaldehyde. Through the article, more information about this compound (cas:2689-65-8) is conveyed.
Furfural diacetate (I) and Br in CHCl3 give 10% of sym-bromofurfural (2-bromo-5-formylfuran), b16 112°, m. 85°; PhNH2 in 50% AcOH gives a characteristic orange-red color; oxime, m. 101°; semicarbazone, m. 215° (corrected, decomposition); phenylhydrazone, m. 80-5°. The di-Et acetal and diacetate could not be prepared Concentrated EtOH-KOH gives bromopyromucic acid. Improved directions are given for the preparation of tetraiodofuran (67% yield). I in AcOH and Hg(OAc)2 give 82% of a trimercuriacetate compound, containing free Hg(OAc)2 which cannot be removed without decomposition of the Hg compound With 0.35% EtOH-HCl there results 86% of the trimercurichloride, which reacts with I in Et2O to give, among other products, sym-iodofurfural, m. 110°.
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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem