Preparation of 3-benzyloxy-2-pyridinone functional linkers: tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators was written by Gibson, Sarah;Fernando, Rasika;Jacobs, Hollie K.;Gopalan, Aravamudan S.. And the article was included in Tetrahedron in 2015.COA of Formula: C13H14BrNO2 This article mentions the following:
In contrast to 2,3-dihydroxypyridine, the 3-benzyloxy protected derivative, 2 (I), undergoes facile alkylation at ambient temperatures with a variety of functionalized alkyl halides in good yields. This alkylation has been used to prepare a number of linkers that permit the attachment of 3,2-HOPO moieties onto various scaffolds using a wide range of coupling methods. The Mitsunobu reaction of 2 with representative alcs. was found to be of limited value due to competing O-alkylation that led to product mixtures The phthalimide 3j (II) can be converted in two steps to HOPO isocyanate 6 (III) in excellent yields. Isocyanate 6 can be coupled to amines at room temperature or to alcs. in refluxing dichloroethane to obtain the corresponding urea or carbamate linked ligand systems. The coupling of isocyanate 6 with TREN followed by deprotection gave the tris-HOPO 10 (IV), an interesting target as it has both cationic and anionic binding sites. The HOPO hydroxylamine linker 11 (V) was shown to be especially valuable as its coupling with carboxylic acids proceeds with the concomitant generation of an addnl. hydroxamate ligand moiety in the framework. The utility of this linker was shown by the preparation of two mixed HOPO-hydroxamate chelators, 16 (VI) and 19 (VII), based on the structure of desferrioxamine, a well-known trihydroxamate siderophore. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4COA of Formula: C13H14BrNO2).
N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.COA of Formula: C13H14BrNO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary