Extracurricular laboratory: Synthetic route of 111-24-0

Here is a brief introduction to this compound(111-24-0)Electric Literature of C5H10Br2, if you want to know about other compounds related to this compound(111-24-0), you can read my other articles.

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Synthesis called N -Methylated 1,8-Diaminonaphthalenes as Bifunctional Nucleophiles in Reactions with α,ω-Dihalogenoalkanes: A Facile Route to Heterocyclic and Double Proton Sponges, Author is Kolupaeva, Ekaterina V.; Ozeryanskii, Valery A.; Pozharskii, Alexander F., which mentions a compound: 111-24-0, SMILESS is BrCCCCCBr, Molecular C5H10Br2, Electric Literature of C5H10Br2.

The reaction of 1-dimethylamino-8-(methylamino)naphthalene with 1,3-dibromopropane chemoselectively leaded to the product of N, N’-heterocyclization, while in the case of 1,4-dibromobutane and 1,2-bis(bromomethyl)benzene the process resulted in heterocyclization onto the same nitrogen atom with the formation of previously unknown 1-dimethylamino-8-pyrrolidino- and 1-dimethylamino-8-isoindolino-naphthalenes. The same reactions conducted without adding any auxiliary base leaded to the formation of N, N’-linked double proton sponges as a new type of polynitrogen organic receptor. Proceeding as a sequence of quaternization-demethylation-cyclization steps, this heterocyclization process was used to construct six-membered rings (piperidino, morpholino), albeit in lower yields. The ability of 1,2-dibromoethane to brominate N-alkylated 1,8-diaminonaphthalenes was described. It is shown for the first time that a com. available 1,8-bis(dimethylamino)naphthalene (DMAN) can be used as a starting material in a heterocyclization reaction, which via a one-pot approach and in a short time can be converted into 1,5-dimethylnaphtho[1,8- bc]-1,5-diazacyclooctane or 1-dimethylamino-8-(pyrrolidin-1-yl)naphthalene.

Here is a brief introduction to this compound(111-24-0)Electric Literature of C5H10Br2, if you want to know about other compounds related to this compound(111-24-0), you can read my other articles.

Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis