Benzoquinoline amines – Key intermediates for the synthesis of angular and linear dinaphthonaphthyridines

Abstract

A systematic study on the condensation reaction of 2,4-dichlorobenzo[h]quinoline and naphth-1-ylamine in the presence of CuI as catalyst to functionalised mono- and di-substituted (naphthalen-1-yl)benzo[h]quinoline amines was described. Subsequently these mono- and di-substituted amines on polyphosphoric acid catalysed cyclisation reaction with aromatic/heteroaromatic carboxylic acids led to the construction of angular and linear aromatic/heteroaromatic substituted dinaphthonaphthyridines in good yields.

Synthesis, In Vitro Cytotoxicity, and DFT Studies of Novel 2‐Amino Substituted Benzonaphthyridines as PDK1 Inhibitors

“…Recently [34] various metal catalyzed reactions of aryl halide with amine have been developed [35–43] . A comprehensive review of the literature points out that the reaction of 2,4‐dichlorobenzonaphthyridines were aimed to get substituted naphthyridines having biological activity one among them is the amination reaction involving aliphatic and aromatic amines thereby deriving the respective aliphatic and aromatic aminonaphthyridines.…”

“…[12,33] Recently [34] various metal catalyzed reactions of aryl halide with amine have been developed. [35][36][37][38][39][40][41][42][43] A comprehensive review of the literature points out that the reaction of 2,4-dichlorobenzonaphthyridines were aimed to get substituted naphthyridines having biological activity one among them is the amination reaction involving aliphatic and aromatic amines thereby deriving the respective aliphatic and aromatic aminonaphthyridines. With the importance of these compounds in mind, we targeted the synthesis of a system that bio labile 1,6naphthyridines with the expected significant biological activity.…”

Efficient synthesis of benzo[h]carbazol[3,2‐b][1,6]naphthyridines

“…As a result of this, the amination of aryl halides by CuI has received a lot of attention. Tandem annulations, a unique combination of copper(I)iodide, and dimethylformamide have piqued interest due to their ease of use and strong reactivity [13,14].…”

Synthesis of novel benzo naphtho naphthyridines from 2,4‐dicloroquinolines

“…The development of C─N bond formation by the insertion of an amine group with an organic molecule using the copper catalysis method, which is more economical, less toxic, and more sustainable than other transition metal catalysis 19 . Thus, CuI catalyzed amination of aryl and heteroaryl halides has gained much attention and recognition 20 . The tandem annulations, the significant combination of copper(I)iodide and dimethyl sulfoxide (CuI/ Dimethyl sulfoxide (DMSO)) has concerned considerable interest, due to its operational simplicity and high reactivity 21 .…”

“…A detailed survey of the literature points out that the reaction of chloroquinolines was aimed to get substituted quinolines possessing biological activity one among them is the amination reaction involving aromatic amines thereby deriving the respective anilinoquinolines. Research on the chemistry of naphthyridines has expanded considerably in recent years in connection with the fact that biologically active compounds have been detected among the derivatives of these heterocycles 20,23,24 . After viewing the above facts, the object of the present investigation was to study the reaction of 2,4‐dichlorobenzo and 2,4‐dichloroquinolines with aromatic amine derivatives through quinoline amine intermediates to get benzo naphtha naphthyridines.…”