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

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 (SeO2) and thionyl chloride (SOCl2) 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 Rf values reported.The reaction progress was followed by thin layer chromatography (TLC). The synthesized compounds were confirmed by spectral data (I.R, H-NMR, C-MNR). The possible fragmentation pattern of GC/MS for the compounds (III), (Vc) and (VIIg) were reported. ب ريضحت ةديدج تانوزارديهو فش دعاوق ضع ىلع ةيوتحم ةعومجم نيدراثفنوزنبلا / نوديراثفنوزنبلا صخلملا ضماح رضح N ) 4 ليثم 2 ليديريب ( ارثنلاا ن ل ي ك ) I ( لعافت ةطساوب أ ناملو . ث لوح م ةق بكرملا ) I ( ماح ةطساوب ض ددعتملا كيروفسفلا PPA) ( يطعيل 4 ليثم 10 -H وزنب [8,1][b] نيدراثفن 5 أ نو ) II .( بكرملا لموع ) II ( يئانث عم موينيليسلا ديسكوا ) SeO2 ( لينوياثلا ديرولكو ) SOCl2 ( يطعيل 4 ليمروف 10 -H وزنب [8,1][b] نيدراثفن 5 نوا ) III ( و 4 ليثم 5 وزنب ورولك [8,1][b] نيدراثفن IV) ( يلاوتلا ىلع . دنع بكرملا ةلعافم ) III ( ةدع عم أ ضوعم تانيلين ة و أ تانيم يتافيلا ة ىطعا ش دعاوق ف (V) . لعافت ىطعا امنيب بكرملا ) IV ( ملا نيزارديهلا عم يئا لا قتشم ـ 5 ونيزارديه ) VI ( ، يذلا تلاعافت لخدا ةدع عم أ هيدل ا تادي أ تانوزارديهلا يطعيل هيتامور ) VIIa-j .( نقت تمدختسا ةي ايفاركوتامورك ةقبطلا ةقيقرلا ) TLC ( لعافتلا ريس ةعباتمل . امك ةيوايزيفلا تباوثلا تلجس ميقو ) R f .( تصخش ةطساوب ةرضحملا تابكرملا بيكارت ءارمحلا تحت ةعشلاا فيط لثم ةيفيطلا قرطلا ) I.R ( يسيطانغملا يوونلا نينرلا فيطو ) H-NMR,C-NMR ( حضوو ل لمتحملا ؤزجتلا ططخم فيط ةلتكلا ) GC/MS ( ل تابكرمل ) III, Vc, VIIg ( . INTRODUCTION Many Benzonaphthyridine derivatives have current interest due to their planner linear structure (Ivanove et al., 2005). Ullmann synthesis involves the condensation of o-halobenzoic acid with substituted 2-aminopyridine in presence of cupric oxide and anhydrous potassium carbonate to give N-pyridylanthranilic acids (Jameel and Al-Hadedi, 2010). Cyclization of N-pyridylanthranilic acid can be achived by concentrated H2SO4 (Acheson, 1973), polyphosphoric acid (PPA) (Meftah et al., 1994) and POCl3 (Al-Hadedi, 2008) to give different types of tricyclic hetero compounds. The literatures showed that the benzonaphthyridine/ benzonaphthyridone derivatives have versatile biological activities such as antitumor (Chen et al., 1994), trypanocidal (Mefetah et Rafid K. Jameel and Attallah M. Sheat