Facile synthesis of 4-phenylquinolin-2(1H)-one derivatives from N-acyl-o-aminobenzophenones |
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Authors: | Kwanghee Koh Park Jin Joo Lee |
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Affiliation: | Department of Chemistry, Chungnam National University, Yu-Sung-Ku, Taejon 305-764, South Korea |
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Abstract: | An efficient synthesis of 4-phenylquinolin-2(1H)-one derivatives has been achieved in a one-pot reaction from N-acyl-o-aminobenzophenones 1a-c (a: acyl=acetyl; b: acyl=propanoyl; c: acyl=heptanoyl) using NaH as a base. Treatment of 1 with NaH provided the quinolones 2a-c with 62-83% yields, whereas the reaction in the presence of alkyl iodide (alkyl=methyl, ethyl, n-octyl) gave the corresponding N-alkylated quinolones 3a-g in 75-95% yields. The alkylation reaction of 4-phenylquinolin-2(1H)-one 2a with alkyl halide gave a mixture of N-alkylated and O-alkylated products. Comparison of IR and NMR data of the N-alkylated and O-alkylated compounds with those of 2a-c indicated that 2a-c exist as the lactam form. |
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Keywords: | N-Acyl-o-aminobenzophenones 4-Phenylquinolin-2(1H)-one N-Alkyl-4-phenylquinolin-2(1H)-ones 2-Alkoxy-4-phenylquinolines Lactam-lactim tautomeric form |
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