One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tr?ger's bases via a nucleophilic displacement approach?

Organic & Biomolecular Chemistry Pub Date: 2017-08-14 DOI: 10.1039/C7OB01835E

Abstract

We report here a novel one-pot synthetic strategy for the synthesis of a family of N-alkyl-1,8-naphthalimide based Tr?ger's bases via a nucleophilic substitution reaction of a common ‘precursor’ (or a ‘synthon’) N-aryl-1,8-naphthalimide Tr?ger's base heated at 80 °C in neat aliphatic primary amine, in overall yield of 65–96%. This methodology provides an efficient and one-step facile route to design 1,8-naphthalimide derived Tr?ger's base structures in analytically pure form without the use of column chromatography purification, that can be used in medicinal chemistry and as supramolecular scaffolds. We also report the formation of the corresponding anhydride, and the crystallographic analysis of two of the resulting products, that of the N-phenyl-4-amino-1,8-naphthalimide and the anhydride derived Tr?ger's bases.

Graphical abstract: One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tr?ger's bases via a nucleophilic displacement approach
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