Novel synthesis of substituted N-(3-aryl-1,8-naphthyridin-2-yl) and N,N′-bis(3-aryl-1,8-naphthyridin-2-yl)benzene-1,4-diamines and 2-(4-((3-aryl-1,8-naphthyridin-2-yl)amino)phenyl)isoindoline-1,3-diones and their biological evaluation

ABSTRACT

A straightforward and highly efficient series of new substituted 3-aryl-1,8-naphthyridine derivatives 3a–e, 4a–e, and 6a–e were synthesized. Condensation dissimilar quantities of 2-chloro-3-aryl-1,8-naphthyridine 1a–e with benzene-1,4-diamine 2 and sodium ethoxide refluxing in ethanol solvent yielded the compounds 3a–e and 4a–e. The 2-(4-((3-aryl-1,8-naphthyridin-2-yl)amino)phenyl)isoindoline-1,3-diones 6a–e were obtained by treatment of compounds 3a–e with phthalic anhydride 5 in refluxing N,N-dimethylformamide is described. All synthesized compounds evaluated for their antimicrobial activity. The structures of the compounds have been proven on the established of spectral (IR, ¹H NMR, and ¹³C NMR) data and elemental analyses. The reaction will be characterized by good efficacy, easy workup, simple purification of the products, and availability of catalyst.

GRAPHICAL ABSTRACT

KEYWORDS:

• 2-(4-((3-Aryl-1,8-naphthyridin-2-yl)amino)phenyl)isoindoline-1,3-dione
• 2-chloro-3-aryl-1,8-naphthyridine
• Antimicrobial activity
• benzene-1,4-diamine
• N,N-dimethylformamide

Acknowledgment

One of the author (Dharavath Ravi) thanks to the UGC, New-Delhi, India for the financial support. Directors, CFRD-OU, IICT-Hyderabad for providing spectral (IR, ¹H NMR, and ¹³C NMR) data and elemental analyses.

Additional information

Funding

This work was supported by the University Grants Committee [Grant Number 23/06/2013(i)EU-V].