One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation was written by Disadee, Wannaporn;Ruchirawat, Somsak. And the article was included in Organic & Biomolecular Chemistry in 2018.Electric Literature of C13H14BrNO2 This article mentions the following:
A one-pot, metal-free process for the synthesis of azabicycles is developed. The key transformations involved a cascade of double intramol. cyclizations via the nitro-Mannich reaction and N-alkylation, providing various ring systems of azabicycles in yields up to 81% and an isomeric ratio of 62 : 1. This approach offers considerable advantages in terms of the handling of small mols., the flexibility to introduce a functionalized side chain, and gives direct access to various azabicycles. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Electric Literature of C13H14BrNO2).
N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Electric Literature of C13H14BrNO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary