Biochem. Cell. Arch. Vol. 18, No. 1, pp. 819-828, 2018 www.connectjournals.com/bca ISSN 0972-5075

SYNTHESIS, CHARACTERIZATION OF SOME NEW HETEROCYCLIC COMPOUNDS DERIVATIVES FROM AZO BIS-CHALCONES

Naji M. Ali Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iraq. (Accepted 28 March 2018)

ABSTRACT : The present work deals with the synthesis of new azo compound from reaction between 4-aminobenzene sulfonamide with acetylacetone, then azo compound reacts with p-dimethyl amino benzaldehyde and p-nitrobenzal dehyde in absolute ethanol to prepare chalcone derivatives. The chalcone derivatives reacts with deferent compounds such as urea, thiourea, guanidin, Meldrum’s acid, barbituric acid to prepare new heterocyclic compound. Key words : Azo compound, chalcone derivatives, heterocyclic compounds.

INTRODUCTION Experimental Azo compounds and its complexes are a very All chemicals were of highest purity and used as important class of chemical compounds receiving attention supplied by the manufactures. Measurements of melting in scientific research; these compounds are explored for points (m.p.) of the synthesized compounds were their applications in different field (Kumar et al, 2009; determined in open capillary tube and thin layer Aspinall, 2002). Biological importance of azo compounds chromatography (T.L.C) was performed on silica gel for is well known for their use as antineoplastics, (T.L.C) and spots were visualized by Iodine vapors. antidiabetics, antiseptics, anti-inflammatory and other Preparation of azo compounds (F & L) useful chemotherapeutic agents (Bae et al, 2003). 4-aminobenzilinde and 2-amino-5-mercpto-1,3,4- The name “Chalcone” was given by Kostanecki and thiadiazole (0.01 mole) was dissolved in 2 ml of Tambor. Also chalcones are well known intermediates for concentrated hydrochloric acid and 20 ml of distilled synthesizing various heterocyclic compounds (Venkatesan water. The solution was cold at 0–50C in ice-water bath. and Sumathi, 2010). Chalcones can be isolated from The sodium nitrite (0.01mole) was dissolved in (10 ml) several plants and are precursors of flavones compounds, of distilled water and added drop wise to the solution with they are similar to enamines, they contain a double bond stirring. Acetyl acetone ( 0.01mole) was dissolved in (20 and prepared from intervention condensation reaction with ml) of ethanol and 5 ml of 10% sodium hydroxide and urea or thiourea and other organic nitrogen compounds cooled to 0–50C, which added to the diazonium solution to form heterocyclic compounds (Hasan and Rasheed, in drope wise and stirring at 0–50C for 2 hours for 2007). The reaction should carried out with strong basic obtaining the coupling agent. The result compound was conditions and low temperatures to yield compounds used precipitated, filtered and washed well with ethanol. in pharmaceutical and an industrial purposes (Palleros, (E)-4-((2,4-dioxopentan-3-yl)diazenyl-N- 2008; Faqrodoin et al, 2012; Sundararajan et al, 2013). phenylbenzamide) F Cyclization of chalcones, leading to thiazines, pyrimidines, has been a developing field within the realm of heterocyclic Yield 78.9 %, m. p 200-202°C; 1H-NMR (DMSO): δ δ chemistry for the past several years because of their ready 3.72 (s, 6H, COCH3), 5.83-8.10 (m, 9H) for aromatic accessibility and the broad spectrum of pharmacological ring, δ 9.89 (s, 1H, CONH), δ 3.90 (s, 1H) for (HC- activities (Vibhute and Basser, 2003; Bhat et al, 2005; C=O); 13C-NMR (DMSO):: 116.21, 120.23, 122.50, Kalirajan et al, 2007; Urmila et al, 2005; Pandey et al, 127.94, 135.44, -145.84(C) Phenyl ring, 87.84 C-12, 2004; Rakesh and Abdul, 2003) as antibacterial, 149.72 C(CO-NH), 151.24-154.70 C (C=O), 27.21 –1 antifungal, antiprotozoal, anti-inflammatory substances C(CH3), 57.14 C(CH-C=O); IR: (N-H)3444.87cm ,(C- (Asiri and Khan, 2011). H, aliphatic) 2950.89cm–1, (C-H, aromatic) 3053.46 cm– 1, (N=N) 1600.92 (C=O amide) 1653.00 cm–1, (C=O