The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ) is researched.Quality Control of 5-Iodo-2-furaldehyde.Novikov, V. N.; Borodaev, S. V.; Babeshkina, L. D. published the article 《Mechanism of the reaction of furan aldehydes with secondary amines in methanol》 about this compound( cas:2689-65-8 ) in Khimiya Geterotsiklicheskikh Soedinenii. Keywords: furfural halo reaction amine mechanism; piperidine reaction halofurfural mechanism; morpholine reaction halofurfural mechanism; furfurylideneammonium halide preparation mechanism; aminal halofurfural intermediate. Let’s learn more about this compound (cas:2689-65-8).
A kinetic study showed that reaction of 5-iodofurfural (I) with piperidine in dilute solution is characterized by an induction period, during which an equilibrium between the starting materials and an intermediate is established. The reaction involves noncatalytic and piperidine-catalyzed paths to form aminal II (X = CH2). In the reaction of I with morpholine, the initial equilibrium between starting materials and intermediate is established instantaneously, and the reaction follows only a morpholine-catalyzed path to form II (X = O). I conversion to iminium salts III (X = CH2, O) was studied in concentrated solutions, and the isolation of aminal intermediates IV (X = CH2, O) was described. The bromo analogs were also studied.
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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem