3-N-丙酰基-2-芳基-5-(3-碘苯基)-1,3,4-(口恶)唑啉类化合物的合成及表征

以3-碘苯甲酸为原料,在浓硫酸作用下与乙醇反应制得3-碘苯甲酸乙酯(1),再以无水乙醇为溶剂,在105℃化合物1与80％的水合肼反应8 h,制得3-碘苯甲酰肼(2)。在无水乙醇中,在90～95℃化合物2分别与4-甲基苯甲醛、2-氯苯甲醛、4-氯苯甲醛、4-羟基苯甲醛、2,4-二氯苯甲醛、4-甲氧基苯甲醛、3-硝基苯甲醛、4-硝基苯甲醛和4-二甲氨基苯甲醛反应得到相应的酰腙3(a～i)]。最后化合物3(a～i)分别与丙酸酐脱水环化成了3-N-丙酰基-2-芳基-5-(3-碘苯基)-1,3,4-(口恶)唑啉类化合物4(a～i)],收率分别为86．2％,70．5％, 80．1％,68．2％,62．4％,75．2％,73．2％,70．5％和63．2％。并通过元素分析,IR,1H NMR和MS对化合物4(a～i)的结构进行了表征。

SYNTHESIS OF 3-N-PROPANOYL-2-ARYL-5-(3-IODOPHENYL)-1, 3, 4-OXADIAZOLINES

Ethyl 3-iodobenzoate (1) was prepared by reaction of 3-iodobenzoic acid with anhydrous eth-anol in the presence of concentrated sulfuric acid. This compound reacted with 80% hydrazine hydrate for 8 h in the presence of anhydrous ethanol as solvent at 105℃to give 3-iodobenzoyl hydrazine (2). In the presence of anhydrous ethanol at 90-95℃, 2 reacted, respectively, with 4-methylbenzalde-hyde, 2-chlorobenzaldehyde, 4-chlorobenzaldehyde, 4-hydroxybenzaldehyde 2, 4-dichlorobenzalde-hyde, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde and dimethylaminobenzaldehyde producing corresponding hydrazones 3(a - g)]. Then 3(a - g) cyclodehydrated with propanoic anhydride to afford 3-N-propanoyl-2-aryl-5-(3-iodophenyl)-1, 3, 4-oxadiazolines 4 (a - i)] with the yield of 86. 2%, 70. 5%, 80. 1%,68. 2%, 62. 4%, 75. 2%, 73. 2%, 70. 5% and 63. 2% , respectively. The structures of 4(a-i) were confirmed by elementary analyses, IR, 1H NMR, and MS spectroscopy.