Z. Naturforsch. 2012,
67b, 1144 – 1150
doi:10.5560/ZNB.2012-0202
Condensation Reactions of 2-Aminobenzohydrazide with Various Carbonyl Compounds
Kamal M.
El-Shaieb,
Mohamed A.
Ameen,
Fathy F.
Abdel-Latif, and
Asmaa H.
Mohamed
Chemistry Department, Faculty of Science, Minia University, El-Minia, Egypt
Received July 16, 2012 / published online November 12, 2012
Technical iodine was found to catalyze the condensation between 2-aminobenzohydrazide (1) and some aldehydes and ketones in absolute ethanol under mild conditions to afford hydrazone and quinazoline derivatives, respectively. Condensation of 1 with terephthalaldehyde (2) in 1:1 molar ratios afforded the hydrazone 3, while hydrazone 4 was formed on using a double molar ratio of 1. On the other hand, compound 1 condensed with 4-formyl [2.2]paracyclophane (5) to give the hydrazone 6. However, spiro-quinazolines 8, 10, 12, and 14 were formed when compound 1 reacted with ketones such as N-benzylpiperidone (7), indane-1,2,3-trione (9), cyclohexane-1,2-dione (11), and dimedone (13), respectively. Treatment of 1 with tetrabromophthalic anhydride (TBPA, 18) and pyromellitic
dianhydride (PMDA, 20) furnished phthalazino-quinazoline 19 and 21, respectively. The products were fully characterized according to their spectral analyses. The mechanisms of formation of the products have been rationalized.
Key words: Quinazolines, Aminobenzohydrazide, Aldehydes, Ketones, Anhydrides, Hydrazones