Synthesis and Cyclization of some N-(2-Pyridyl) Anthranilic Acids

AL-Hadedi, Azam A.; Jameel, Rafid K.

doi:10.33899/rjs.2010.36807

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RJS

2010

DOI: 10.33899/rjs.2010.36807

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Synthesis and Cyclization of some N-(2-Pyridyl) Anthranilic Acids

Azam A. AL-Hadedi¹,

Rafid K. Jameel²

Abstract: A series of N-(2-Pyridyl) anthranilic acids (Ia-f) have been synthesized by Ullmann reaction. Cyclization of (Ib,d,f) by phosphorusoxy chloride (POCl 3) gives substituted 5chlorobenzo [b][1,8] naphthyridine compounds. The reaction progress was followed by thin layer chromatography (TLC), rate flow (R f) values was recorded, spectral data (IR) and (U.V) were recorded. Elemental analysis (CHNS) and gas chromatography-mass spectrometery (GC/MS) were carried out for some of the synthesized compounds.

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2014

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Synthesis of some New Schiff Bases and Hydrazones Containing Benzonaphthyridine/ Benzonaphthyridone Moiety

Jameel¹,

Sheat²

2014

RJS

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The N-(4-methyl-2-pyridyl)anthranilic acid (I) was synthesized by Ullmann condensation. The compound (I) was cyclized by polyphosphoric acid (PPA) to give 4-methyl-10Hbenzo[b][1,8]naphthyridin-5-one (II). The compound (II) was treated with selenium dioxide (SeO 2) and thionyl chloride (SOCl 2) to give the 4-formyl-10H-benzo[b][1,8]naphthyridin-5-one (III) and 4methyl-5-chloro-benzo[b][1,8]naphthyridine (IV) respectively.The compound (III) was reacted with various substituted anilines and aliphatic amines to give the Schiff bases (Va-j). The compound (IV) was reacted with hydrazine hydrate to yield the 5-hydrazino derivative (VI), which was reacted with various aromatic aldehydes to yield the hydrazones (VIIa-j) and the R f values reported.The reaction progress was followed by thin layer chromatography (TLC). The synthesized compounds were confirmed by spectral data (I.R, 1 H-NMR, 13 C-MNR). The possible fragmentation pattern of GC/MS for the compounds (III), (Vc) and (VIIg) were reported.

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Synthesis of some New Schiff Bases and Hydrazones Containing Benzonaphthyridine/ Benzonaphthyridone Moiety

Jameel¹,

Sheat²

2014

RJS

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Synthesis and Cyclization of some N-(2-Pyridyl) Anthranilic Acids

Cited by 1 publication

References 10 publications

Synthesis of some New Schiff Bases and Hydrazones Containing Benzonaphthyridine/ Benzonaphthyridone Moiety

Synthesis of some New Schiff Bases and Hydrazones Containing Benzonaphthyridine/ Benzonaphthyridone Moiety

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