Synthesis of new calgone and amide derivatives of 3-amino-2-acetylbenzofuran

ABSTRACT Master Thesis SYNTHESIS OF NEW CALGONE AND AMIDE DERTVATIES OF 3-AMINO -2- ACETYLBENZOFURAN Neslihan KEÇECİ Fırat University Graduate School of Natural and Applied Sciences,, Department of Chemistry 2005, Page: 67 In this study, 2-hydroxybenzonitrile and 1-chloroacetone were reacted in the presence of K2CO3 for the synthesis of 3-amino-2-acetylbenzofuran. This compound was rearranged with triethylamine to amide via acylchloride (N-Acetyl-3-amino-2-actyl-benzofuran, N-Propionyl-3- amino-2-acetyl-benzofuran, N-(2-Chloroacetyl)-3-amino-2-acetyl-benzofuran, N-Benzoyl-3- amino-2-acetyl-benzofuran, N-(2-Chloro-benzoyl)-3 -amino-2-acetyl-benzofuran, N-(4- Methoxy-benzoyl)-3 -amino-2-aceryl-benzofuran ve N-phenylacetyl-3 -amino-2-acetyl- benzofuran) and rearranged to calgone via aromatic aldehyde in organic solvents (l-(3~Amino- l-benzofuran-2-yl)-3-phenyl-propen-2-en-l-on, l-(3-Amino-l-benzofuran-2-yl)-3-(2-floro) phenyl-propen-2-en- 1 -on, 1 -(3 -Amino- 1 -benzofuran-2-il)-3 -thiöfen-2-il-propen-2-en- 1 -on, 1 - (3-Amino- 1 -benzofuran-2-yl)-3 -(2-piridyl)-propen-2-en- 1 -on ve 1 -(3 -Amino-1 -benzofuran-2- yl)-3-(3-nitrophenyl)-propen-2-en-l-on)).. From this 3-aminocalgones, a new amides were synthesized with phenyl acetylchloride(l-[(N-phenylacetyl)-3-Amino-l-benzofuran-2-yl]-3- phenyl-propen-2-en-l-on ve l-[(N-phenylacetyl)-3-Amino-l-benzofuran-2-yl]-3-(3-nitro- phenyl)-propen-2-en-l-on). Also a new pyrazoline were synthesized from calgone with hydrazinehydrat(3-(3-Aminobenzofuran-2-yl)-4-phenyl-pirazolin). The structures of the compounds were defined by DSC, FT-IR, 'H-NMR spectroscopy and elemental analyses techniques. Keywords: Benzofurane, calgone and'amide