In this paper, we consider the Synthesis of a series of various 4-amino antipyrine derivatives containing 1,3-thiazinan-4-one, 1,3-oxazinan-6-one, and 1,3-oxazepin-4,7-dione in its structure. These derivatives were obtained via cycloaddition of the methenamine group in Schiff base analog of 4-amino antipyrine with 3-mercaptopropanoic acid, 3-chloropropanoic acid, maleic and citraconic anhydride, respectively. The Schiff bases were prepared in excellent yields by condensation of 4-amino antipyrine with 3-nitro- or 3-bromobenzaldehyde in n-butanol. We characterize the desired products by C.H.N.S analysis, FT-IR, and 1HNMR spectroscopy.