取代-1H-吡唑-5-甲酸与取代噻二唑-2-氨的酰胺化合物的合成及生长素活性

采用"一锅法"合成3-(4-甲氧基苯基)-1H-5-吡唑甲酸乙酯,分别将吡唑环上1-位甲基化、4-位氯代后水解,得到2种吡唑羧酸;以取代羧酸和氨基硫脲为原料,三氯氧磷为脱水剂,合成6种5-取代-2-氨基-1,3,4-噻二唑化合物;再将吡唑结构单元及1,3,4-噻二唑结构单元以酰胺键结合在一起,合成了12种新的酰胺化合物,目标产物最终收率可达50%以上。用元素分析、IR和1HNMR测试技术确定了其结构。用小麦芽鞘法测试其生长素活性均不高,有的对小麦芽鞘生长显示抑制作用。

Synthesis and Auxin Activities of Acylamides with Substituted-1H-pyrazole-5-formic Acid and Substituted Thiadiazole-2-ammonia

Ethyl 3-(4-methoxy phenyl)-1H-pyrazole-5-carboxylate was synthesized by means of one-pot reaction method; and two kinds of pyrazole carboxylic acid were obtained through methylation at position 1, chlorination at position 4 and hydrolysis. Six 5-substituted-2-amino-1,3,4-thiadiazoles were obtained from substituted carboxylic acids and thiosemicarbazide using phosphorus acylchloride as the dehydrating agent. Pyrazole and 1,3,4-thiadiazole were connected together by amido bond and 12 new compounds were synthesized. The yield of the title compounds was up to 50%. All the new compounds were confirmed by means of elemental analysis, IR and 1H NMR spectroscopies. Their auxin activities are not high, and a few of them are antiblastic to wheat gemma.